Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.169674-01-5,5,6-Difluoroindole,as a common compound, the synthetic route is as follows.,169674-01-5

Trifluoroacetic anhydride (38 mL, 56.0 g, 0.27 mol) was added dropwise to a solution of 5,6-difluoro-lH-indole (0.22 mol) in DMF (300 mL) over 0.5 h at 0C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was quenched with water (1 L), many solid began to form, the mixture was stirred for 0.5 h, then filtered. The solid was collected, washed with water (200 mL><3), then added to aqueous sodium hydroxide (20%, 150 mL, 0.75 mol) and heated under reflux for 8 h. The reaction mixture was cooled and acidified with aqueous 3N HC1 to pH of 3. Many solid began to form. The solid was collected by filter, washed with water (200 mL><3), dried to give title compound 91-1 (15.53 g, 59% yield). 169674-01-5 5,6-Difluoroindole 2778732, aindole-building-block compound, is more and more widely used in various fields. Reference£º
Patent; ARIAGEN, INC.; COLABUONO, Peter; JOHNSON, Graham; MANNING, David Douglas; WOLF, Mark Allan; (312 pag.)WO2019/99977; (2019); A2;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

50820-65-0, Methyl 1H-indole-6-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Compound 2 (5 mmol) was added to hydrazine- hydrate (80) (3 mL)at room temperature, and the mixture was irradiated continually for 5-8 min at 300 W. The reaction progress was monitored by TLC. After the reaction was complete and the mixture was sufficiently cooled, intermediate 3 (yield 83-98) was formed., 50820-65-0

50820-65-0 Methyl 1H-indole-6-carboxylate 639844, aindole-building-block compound, is more and more widely used in various fields.

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Article; Ye, Ying; Suo, Yourui; Yang, Fang; Yang, Yongjing; Han, Lijuan; Journal of Chemical Research; vol. 39; 5; (2015); p. 296 – 299;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.93247-78-0,Methyl 1H-indole-7-carboxylate,as a common compound, the synthetic route is as follows.,93247-78-0

Example 17; Preparation of Al3; Indole-7 carboxyldehyde (K-44); Methyl 7-indolecarboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. VoI HV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in anhydrous THF (250 niL) was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2h. After cooling to room temperature, the excess hydride was quenched by addition of water (12mL), 15% NaOH (12mL) and water (26mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (lH-indol-7-yl)- methanol (10.7 g, 98%). 1HNMR (CDCl3). To a solution of the alcohol, (IH- indol-7-yl)-methanol (8.0 g, 54.3 mmol) in 400 mL of methylene chloride was added activated manganese (IV) oxide (85%, 41.0 g, 0.40 mol), and stirred at ambient temperature for 72h. After additional of 200 mL of methylene chloride and 400 mL of methanol to the reaction mixture, the whole mixture was filtered through a pad of silica gel to remove solid materials. The filtrate was concentrated to afford a crude product, which was purified by a column chromatography on silica gel to yield lH-indole-7-carbaldehyde, K-44 (6.55 g, 83%).

The synthetic route of 93247-78-0 has been constantly updated, and we look forward to future research findings.

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Patent; DECODE CHEMISTRY, INC.; WO2006/44415; (2006); A2;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

3468-17-5, (1H-Indol-6-yl)methanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 76: Preparation of N-((lH-indol-6-yl)methyl)-5-(4-((2-oxopyridin-l(2H)- yl)methyl)benzyl)nicotinamide A mixture of 5-(4-((2-oxopyridin-l(2H)-yl)methyl)benzyl)nicotinic acid (91 mg, 0.28 mmol, 1.0 eq.), (1H- indol-6-yl)methanamine (44 mg, 0.30 mmol, 1.07 eq.), HATU (114 mg, 0.3 mmol, 1.07 eq.) and DIPEA (0.5 mL) in DCM (3 mL) was stirred at rt overnight. Filtered and the solid was collected and triturated with water to afford N-((lH-indol-6-yl)methyl)-5-(4-((2-oxopyridin-l(2H)-yl)methyl)benzyl)nicotinamide as a white solid (100 mg, 78.7%). LRMS (M+H+) m/z calculated 449.2, found 449.2. NMR (CD3OD, 400 MHz) delta 8.85 (s, 1 H), 8.57 (s, 1 H), 8.09 (s, 1 H), 7.69 (d, 1 H), 7.55-7.51 (m, 2 H), 7.39 (t, 1 H), 7.29-7.22 (m, 5 H), 7.03 (d, 1 H), 6.57 (d, 1 H), 6.43-6.37 (m, 2 H), 5.18 (s, 2 H), 4.67 (s, 2 H), 4.08 (s, 2 H).

3468-17-5, As the paragraph descriping shows that 3468-17-5 is playing an increasingly important role.

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Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2591-98-2,2-(1H-Indol-3-yl)acetaldehyde,as a common compound, the synthetic route is as follows.

At O0C under argon, lithium aluminum hydride (14 mg, 0.00036 mol) was added to a solution of intermediate 7 (74 mg, 0.00036 mol) in THF (1 ml). The mixture was stirred at 0C for 1 hour, quenched with a 5% solution of potassium hydrogen sulfate, and extracted twice with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was evaporated, to give the indole-3-yl acetaldehyde as an orange oil. A mixture of intermediate 9 (200 mg, 0.00074 mol) and sodium cyanoborohydride (64 mg, 0.0010 mol) in MeOH (2.3 ml) and acetic acid (2 drops) was added dropwise to a solution of the previous aldehyde (236 mg, 0.0015 mol) in MeOH (2 ml). The reaction mixture was stirred at room temperature for 16 hours. The reaction was quenched with water, made alkaline with a saturated solution of sodium hydrogen carbonate and extracted 3 times with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (40-63 mum) (eluent: EtOAc/MeOH 100/0 to 90/10). The pure fractions were collected and the solvent was evaporated, yielding 190 mg (44 %) of compound 3 as an orange foam.1H NMR (300 MHz, CDCl3) delta 8.42 (d, IH, J=5.7), 8.08 (brs, IH), 7.79 (d, IH, J=2.4), 7.63 (d, IH, J=7.8), 7.40 (d, IH, J=8.1), 7.25-7.07 (m, 5H), 6.59 (s, IH), 6.48 (dd, IH, J=8.7. J=2.1), 4.00 (m, 5H), 3.48 (t, 2H, J=6.8), 3.12 (m, 4H). MS (ES+) w/z 413 (M+l).

2591-98-2, As the paragraph descriping shows that 2591-98-2 is playing an increasingly important role.

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Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/107545; (2007); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.858515-65-8,4-Methyl-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

858515-65-8, A procedure for converting quinuclidin-4-ylmethyl 4-methyl-l//-indole-3-carboxylate phosphate salt (93% assay purity; mix of polymorphs) to quinuclidin-4-ylmethyl 4-methyl-lH- indole-3-carboxylate phosphate salt (polymorphic Form A) is shown in Scheme 1. step 1: A solution of 4-methyl-lH-indole-3-carboxylic acid (1.88 kg) in DMF (0.54 kg) I was added to DCM (63 kg) in a reactor. The system was vacuumed and refilled with N2 for three cycles. The solution was heated to 25-35 C (internal temperature). Oxalyl chloride (2.7 kg) Lambda was added drop-wise over 2 hr while maintaining the temperature at 25-35 C under nitrogen. The mixture was stirred for 4 hrs at 25-35 C under nitrogen. The reaction mixture was concentrated under vacuum (0.08 Mpa) at 30-35 C to about 15-20 L and evaporated at 35 ¡À 5 C using a rotary evaporator to remove DCM and oxalyl chloride until an obvious distillate was observed. The reaction mixture was charged with DCM (15.0 kg) and evaporated to dryness, and this charge-evaporate procedure was repeated for two cycles. Fifteen kilograms of DCM was charged to the mixture and stirred to obtain a clear solution, and an additional 15 kg of DCM was charged to the mixture in the rotary evaporator. The solution in the rotary evaporator was transferred to a dropping tank under nitrogen. Quinuclidin-4-ylmethanol N-borane complex (1.5 kg) and Et3N (1.65 kg) were added to a reactor containing DCM (15.0 kg). The mixture was cooled to 0-5 C (internal temperature), and the solution from the dropping tank in the previous step was added over 2 hrs under nitrogen at 0-5 C. The mixture was heated to 15-25 C with stirring and was stirred at 15- 25 C for 16 hrs under nitrogen. Saturated NH4CI solution (20.3 kg) was added dropwise to quench this reaction at 15-25 C. The mixture was stirred for 30 min and settled aside for 15 min. The organic layer was separated and washed with brine (40.8 kg) and dried with anhydrous Na2SC4 (3.0 kg). The solid was filtered, and the cake was washed with DCM (3.0 kg).

The synthetic route of 858515-65-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ALPHARMAGEN, LLC; NG, John, Sau-Hoi; NG, Raymond; (86 pag.)WO2017/120532; (2017); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

348640-06-2, 4-Bromo-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine A mixture of 4-bromo-1H-pyrrolo[2,3-b]pyridine (10.0 g, 51.0 mmol), Pin2B2 (15.5 g, 61.0 mmol), PdCl2(dppf) (2.0 g, 2.5 mmol) and KOAc (10.0 g, 102 mmol) in 1,4-dioxane (200 mL) was degassed with Ar for 5 minutes. The reaction mixture was heated to 80 C. and stirred for 16 h. The mixture was cooled to RT, filtered through CELITE and concentrated under reduced pressure. The residue was purified via silica gel chromatography (0-25% EtOAc in hexanes) to afford the title compound (3.8 g, 31% yield) as a white solid. MS (ES+) C13H17BN2O2 requires: 244, found: 245 [M+H]+., 348640-06-2

The synthetic route of 348640-06-2 has been constantly updated, and we look forward to future research findings.

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Patent; Board of Regents, The University of Texas System; DI FRANCESCO, Maria Emilia; JONES, Philip; CARROLL, Christopher Lawrence; CROSS, Jason Bryant; RAMASWAMY, Suyambu Kesava Vijayan; JOHNSON, Michael Garrett; LIVELY, Sarah; LAPOINTE, David; US2019/16713; (2019); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4769-96-4,6-Nitro-1H-indole,as a common compound, the synthetic route is as follows.,4769-96-4

A solution of 6-nitro-1H-indole (1.0 g, 6.17 mmol) in tetrahydrofuran (5 mL) cooled to 0 C. was treated with trifluoroacetic anhydride (1.31 mL, 9.25 mmol). The reaction was stirred at 0 C. for 1 h and then was allowed to warm to 25 C. where it was stirred for 16 h. At this time, the reaction was poured into water (100 mL) and stirred at 25 C. for 5 min. The resulting precipitate was collected by filtration, washed with water (100 mL), and dried in vacuo. This solid was re-dissolved in tetrahydrofuran (8 mL) at 25 C., and the resulting solution was treated with trifluoroacetic anhydride (1 mL, 7.08 mmol) and was stirred at 25 C. for 1 h. The resulting precipitate was collected by filtration, washed with water, and dried in vacuo to afford 2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)-ethanone (646 mg, 40%) as a yellow solid: mp 263-265 C.; EI-HRMS m/e calcd for C10H5F3N2O3 (M+) 258.0252, found 258.0253. [0060] A solution of 2,2,2-trifluoro-1-(6-nitro-1H-indol-3-yl)-ethanone (1.0 g, 3.87 mmol) in N,N-dimethylformamide (10 mL) at 25 C. was treated with potassium carbonate (1.34 g, 9.68 mmol). The resulting mixture was stirred at 25 C. for 10 min and then treated with 2-iodopropane (0.58 mL, 5.81 mmol). The reaction was heated at 65 C. for 3 h. At this time, the reaction was cooled to 25 C. and was partitioned between water (50 mL) and ethyl acetate (50 mL). This mixture was treated with a 1N aqueous hydrochloric acid solution (25 mL). The organic layer was washed with water (1¡Á50 mL) and a saturated aqueous sodium chloride solution (1¡Á50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 2,2,2-trifluoro-1-(1-isopropyl-6-nitro-1H-indol-3-yl)-ethanone (581 mg, 98%) as a yellow solid: mp 143-145 C.; EI-HRMS m/e calcd for C14H14F3NO (M+) 269.1027, found 269.1037. [0061] A solution of 2,2,2-trifluoro-1-(1-isopropyl-6-nitro-1H-indol-3-yl)-ethanone (525 mg, 1.75 mmol) in a 20% aqueous sodium hydroxide solution (10 mL) was heated at 1110 C. for 2 h. At this time, the reaction was cooled to 25 C., partitioned between water (75 mL) and ethyl acetate (75 mL), and treated with a 1N aqueous hydrochloric acid solution (25 mL). The organic layer was washed with water (1¡Á50 mL) and a saturated aqueous sodium chloride solution (1¡Á50 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 1-isopropyl-6-nitro-1H-indole-3-carboxylic acid (436 mg, 99%) as a yellow solid: mp 242-243 C.; EI-HRMS m/e calcd for C12H12N2O4 (M+) 248.0797, found 248.0796. [0062] A solution of 1-isopropyl-6-nitro-1H-indole-3-carboxylic acid (200 mg, 0.81 mmol) in methylene chloride (4 mL) and NN-diisopropylethylamine (0.32 mL, 1.85 mmol) at 25 C. was treated with benzotriazol-1-yloxy-tris(dimethylamino) phosphonium hexafluoro-phosphate (463 mg, 1.05 mmol). The reaction was stirred at 25 C. for 20 min. At this time, the reaction was treated with 2-aminothiazole (186 mg, 1.85 mmol) and was stirred at 25 C. for 24 h. At this time, the reaction mixture was partitioned between water (50 mL) and ethyl acetate (50 mL) and was treated with a 1N aqueous hydrochloric acid solution (25 mL). The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was dissolved in a hot solution of 1/1 hexanes/ethyl acetate and then filtered. The filtrate was cooled in the freezer for 1 h. At this time, the resulting solid was collected by filtration. The filtrate was concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 1/1 hexanes/ethyl acetate) afforded 1-isopropyl-6-nitro-1H-indole-3-carboxylic acid thiazol-2-ylamide (13 mg, 4.9%) as a yellow solid: mp 236-239 C.; EI-HRMS m/e calcd for C15H14N4O3S (M+) 330.0786, found 330.0792.

As the paragraph descriping shows that 4769-96-4 is playing an increasingly important role.

Reference£º
Patent; Corbett, Wendy Lea; US2004/67939; (2004); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1204-06-4,3-Indoleacrylic Acid,as a common compound, the synthetic route is as follows.

General procedure: To a solution of the acid derivative (1mmol) in CH2Cl2 were added triethylamine (2mmol) and ethyl chloroformate (1mmol), followed by stirring at 0C for 30min. After addition of the appropriate amine derivative (1.2mmol), the mixture was stirred for an additional 1h at 0C. Then, the reaction mixture was warmed to room temperature and stirred overnight. After the solvent was evaporated under reduced pressure, acetone was added, filtered, and evaporated. The residue was dissolved in CH2Cl2, and the organic phase was washed with a 1% NaHCO3 solution and brine, dried over Na2SO4, and evaporated under vacuum. The final residue was purified by flash column chromatography (Combiflash Rf) using CH2Cl2-MeOH (0-5%) as eluents. 4.3.9 (E)-N-(2,4-Dimethoxybenzyl)-3-(1H-indol-3-yl)acrylamide 3i Yield 48%, mp 164-166 C; IR (FTIR/FTNIR-ATR): 1644 cm-1 (C=O), 3241 cm-1 (N-H). 1H NMR (DMSO-d6) delta: 11.54 (1H, s), 8.07 (1H, t, J = 6 Hz), 7.92 (1H, d, J = 8 Hz), 7.74 (1H, s), 7.61 (1H, d, J = 15.6 Hz), 7.45 (1H, d, J = 7.6 Hz), 7.18 (3H, m), 6.71 (1H, d, J = 16 Hz), 6.57 (1H, s), 6.50 (1H, d, J = 8 Hz), 4.28 (2H, d, J = 5.6 Hz), 3.81 (3H, s), 3.74 (3H, s). 13C NMR (DMSO-d6) delta: 166.9, 160.4, 158.4, 138.0, 133.6, 131.0, 129.8, 125.5, 122.8, 120.9, 120.7, 119.8, 116.9, 112.9, 112.8, 104.9, 98.8, 56.0, 55.8, 37.7; HRMS C20H21N2O3 [M+H]+ Calcd 337.1552, Found m/z 337.1539., 1204-06-4

As the paragraph descriping shows that 1204-06-4 is playing an increasingly important role.

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Article; Baytas, Sultan Nacak; Inceler, Nazan; Yilmaz, Akin; Olgac, Abdurrahman; Menevse, Sevda; Banoglu, Erden; Hamel, Ernest; Bortolozzi, Roberta; Viola, Giampietro; Bioorganic and Medicinal Chemistry; vol. 22; 12; (2014); p. 3096 – 3104;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

30218-58-7, N,N-Dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

30218-58-7, General procedure: PCC (1.1 mmol) was added to a stirred solution of 4 (1mmol) in DMF (5 mL) at 100 C (pre-heated oil bath) and the mixture was stirred at 100 C for 0.5 h.After cooling, the resulting mixture was added to 10% aqueous HCl solution, extracted with AcOEt (100mL), washed with brine, and dried over MgSO4. The solvent was removed, and the residue was purifiedby silica gel column chromatography with CH2Cl2 to give 2.

The synthetic route of 30218-58-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Itoh, Tomoki; Abe, Takumi; Nakamura, Shuhei; Ishikura, Minoru; Heterocycles; vol. 91; 7; (2015); p. 1423 – 1428;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles