Month: March 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6127-19-1,6-Bromo-2-methyl-1H-indole,as a common compound, the synthetic route is as follows.

6127-19-1, To a 100 mL round-bottom flask purged with N2 was placed a solution of 6-bromo-2- methyl-1H-indole (1.00 g, 4.76 mmol) and DMAP (58 mg, 0.47 mmol) in THF (15 mL), followed by the addition of Boc2O (1.565 g, 7.17 mmol). The resulting solution was stirred at rt for 2 h then the solvent was removed under reduced pressure. The crude product was purified by column chromatography affording 1.32 g (89%) of the title compound as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C14H17BrNO2: 310; found: 310 [M+H].

6127-19-1 6-Bromo-2-methyl-1H-indole 271554, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; PROTEOSTASIS THERAPEUTICS, INC.; CULLEN, Matthew; BASTOS, Cecilia M.; PARKS, Daniel; MUNOZ, Benito; (0 pag.)WO2020/6296; (2020); 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.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

General procedure: General procedure (10): To a solution of aminoindole (1.0 equiv) and triethylamine (3.6 equiv) in dichloromethane (10 ml_ for 1.182 mmol of starting material), acetyl chloride (1.2 equiv) was added. The reaction was stirred at room temperature for 3 h. The mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated in vacuo. Purification by flash silica gel column chromatography afforded the indole-acetamide product. Intermediate 17 A/-(1/-/-indol-5-yl)acetamide Intermediate 17 (177 mg, 1.016 mmol) was prepared as a clear oil from Intermediate 16 (156 mg, 1.182 mmol) according to general procedure (10) using 7:3 hexane/ethyl acetate as the eluent for flash silica gel column chromatography. Yield: 85%. 1H NMR (400 MHz, CDCI3) delta 8.27 (bs, 1 H), 7.80 (s, 1 H), 7.30 (d, J = 8.5 Hz, 2H), 7.20 (dd, J = 8.8, 2.0 Hz, 2H), 6.50 (s, 1 H), 2.18 (s, 3H)., 5192-03-0

The synthetic route of 5192-03-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; NATIONAL UNIVERSITY OF SINGAPORE; LEE, Sang Hyun; DYMOCK, Brian William; KITAGAWA, Mayumi; SEE, Cheng Shang; (178 pag.)WO2016/200339; (2016); 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

2795-41-7, 6-Fluoroindole-3-carboxaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2795-41-7, General procedure: Piperidine (0.08 mL) was added to methanol (25 mL) dissolved in substituted aldehydes 5-7 (0.18 mmol) and starting 2-indolinone derivatives 8-11 (0.18 mmol) which were prepared as described previously refPreviewPlaceHolder[6], refPreviewPlaceHolder[21], refPreviewPlaceHolder[22], refPreviewPlaceHolder[23], refPreviewPlaceHolder[24] and refPreviewPlaceHolder[25]. The mixture was refluxed for 5 h. For the targeted compounds 12-21 and 28-36, the mixture was evaporated to remove the solvent and the residue was purified by column chromatography (CH2Cl2/MeOH 100:1-10:1). For the targeted compounds 22-27, ethyl ether (15 mL) was added to the residue and the yellow precipitate was collected by filtration. The obtained precipitate was subjected to the hydrogen chloride saturated methanol to afford it as hydrochloride derivative. All the targeted compounds 12-36 show moderate to good yields under this reaction condition with the yields of 60-92%.

As the paragraph descriping shows that 2795-41-7 is playing an increasingly important role.

Reference：
Article; Zou, Hongbin; Zhang, Liang; Ouyang, Jingfeng; Giulianotti, Marc A.; Yu, Yongping; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5970 – 5977;,
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

14618-45-2, 3-(Trifluoroacetyl)indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a chilled (-780C) solution of 241 mg (1.13 mmol) of 2,2,2-trifluoro-l-(lH-indol-3- yl)ethanone in 5 mL of anhydrous TetaF was added 45 mg (1.13 mmol) of 60% NaH in mineral oil. In another flask, 452 muL (1.13 mmol) of n-BuLi was then added to a chilled (-780C) solution of 310 mg (1.13 mmol) of 5-bromo-l-pyridin-3-yl-lH-indazole in 10 mL of TetaF. After 1 minute, the sodium salt of 2,2,2-trifluoro-l-(lH-indol-3-yl)ethanone was added to the indazole anion via a cannula. After 1 hour, the mixture was diluted with 25 mL of saturated aqueous ammonium chloride and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with three 10 mL portions of brine, dried over magnesium sulfate, filtered and concentrated. The crude material was purified using Combiflash chromatography using EtOAc -hexanes (0-70% gradient) to afford 45 mg (10%) of 2,2,2-trifluoro-l-(lH-indol-3-yl)-l-(l-pyridin-3-yl-lH-indazol-5-yl)ethanol as a colorless solid.

14618-45-2, As the paragraph descriping shows that 14618-45-2 is playing an increasingly important role.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/70507; (2008); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.213682-04-3,4-Methoxy-1H-indole-2-carbaldehyde,as a common compound, the synthetic route is as follows.

Example 84 COMPOUND IN-076 3-(4-Methoxy-1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide A mixture of 2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid methylamide (194 mg, 0.86 mmol), 4-methoxy-1H-indole-2-carbaldehyde (150 mg, 0.86 mmol) and piperidine (36 mg, 0.43 mmol) in ethanol (0.2M) was stirred at room temperature for a total of 5 days. The reaction was concentrated to 1/4 of its volume and the precipitate was collected by vacuum filtration to give the title compound as a pale orangish-red solid. 1H-NMR (360 MHz, DMSO-d6) delta 12.82 (s, 1H, NH), 11.36 (br s, 1h, NH), 8.11(s, 1H-H-vinyl), 8.11 (d, J=1.3 Hz, 1H), 7.63 (dd, J=1.3 & 8.5 Hz, 1H), 7.15-7.27 (m, 4H), 7.08 (d, J=7.96 Hz, 1H), 6.56 (d, J=7.7 Hz, 1H), 3.92 (s, 3H, OCH3), 2.43 (d, J=5.02 Hz, 3H, NCH3). MS m/z 384 [M++1].

213682-04-3, 213682-04-3 4-Methoxy-1H-indole-2-carbaldehyde 10678838, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Tang, Peng Cho; Harris, G. Davis; Li, Xiaoyuan; US2002/52369; (2002); 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

10601-19-1, 5-Methoxy-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 5-methoxyindole-3-carboxaldehyde (80 g) in dimethylformamide (1 L) under nitrogen was treated portion-wise with sodium hydride (20.1 g, 60% dispersion in mineral oil) over 15 minutes. After stirring at ambient temperature for 30 minutes the mixture was treated dropwise with methyl iodide (31.3 mL) over 10 minutes and stirring was then continued for a further 2 hours. The reaction mixture was poured cautiously into water then extracted with ethyl acetate. The organic phase was washed with water, then dried over sodium sulfate and then evaporated. The residue was triturated with pentane to give the title compound (76 g) as a pale brown solid, m.p. 133-134 C. 1H NMR [(CD3)2SO]: delta 9.86 (1H, s); 8.20 (1H, s); 7.60 (1H, d, J=2.6 Hz); 7.50 (1H, d, J=8.9 Hz); 6.96 (1H, dd, J=8.9 and 2.6 Hz); 3.86 and 3.80 (6H, s)., 10601-19-1

10601-19-1 5-Methoxy-1H-indole-3-carbaldehyde 82758, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Cox, Paul J.; Majid, Tahir N.; Lai, Justine Y.Q.; Morley, Andrew D.; Amendola, Shelley; Deprets, Stephanie D.; Edlin, Christopher; US2004/9983; (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

434958-85-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.434958-85-7,N-Boc-5-Hydroxyindole,as a common compound, the synthetic route is as follows.

To a solution of Intermediate 49 (3.00 g, 12.9 mmol, 1.0 eq) in anhydrous MeCN (13 mL) was added a solution of N-bromosuccinimide (2.53 g, 14.2 mmol, 1.1 eq) in anhydrous MeCN (130 mL) dropwise via cannula. After 1.5 h, addition was complete and the reaction mixture was stirred for a further 1 h. The reactionmixture was concentrated in vacuo and purified twice by silica gel chromatography using hexane/CH2CI2 (1 :0-1 .5:1) to yield Intermediate 50 as a white solid (605 mg, 15%).1H NMR (300MHz, DMSO-d5) oH. 9.95 (5, 1H), 7.78-7.91 (m, 1H), 7.61-7.73 (m, 1H), 6.97 (d, J=8.9 Hz, 1H), 6.50-6.59 (m, 1H), 1.54-1.70 (m, 9H).MS (E5) 311.9 (45%, [M-Hfl.

The synthetic route of 434958-85-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; SILVA, Franck Alexandre; CECIL, Alexander Richard Liam; ALEXANDER, Rikki Peter; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; (123 pag.)WO2017/29521; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6127-17-9,6-Chloro-2-methyl-1H-indole,as a common compound, the synthetic route is as follows.,6127-17-9

To a solution of 0.38 g (2.3 mmol) 6-chloro-2-methyl-1H-indole in 20 ml 1,2-dichloroethane at 0 C. were added 0.35 ml (2.5 mmol) trifluoroacetic anhydride. The reaction mixture was quenched with aqueous 2 M sodium carbonate solution after 30 min and extracted with dichloromethane (3*100 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the title compound (0.57 g; 95%) as an off-white solid. MS m/e (%): 260 (M-H+, 100).

As the paragraph descriping shows that 6127-17-9 is playing an increasingly important role.

Reference：
Patent; Bissantz, Caterina; Grundschober, Christophe; Masciadri, Raffaello; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick; US2008/161315; (2008); 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.393553-57-6,6-Bromo-4-methoxy-1H-indole,as a common compound, the synthetic route is as follows.

To a solution of 6-bromo- 4-methoxy-lH-indole A.85 (2.117 g, 9.36 mmol) in DMF (46 mL) at room temperature was added Cs2CO3 (9.155 g, 28.1 mmol) followed by 4-chloropyrimidin-2-amine A.12 (1.456 g, 11.24 mmol) and the mixture was stirred at 80 0C for 21 hours. The mixture was poured into water (200 mL) and the aqueous layer was extracted with ethyl acetate (100 mL x 2). The combined organic layers were washed with brine (100 mL x 2), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a brown solid. The product was purified by silica gel column chromatography using 65% ethyl acetate in hexane as eluent to give 4-(6- bromo-4-methoxy-lH-indol-l-yl)pyrimidin-2-amine A.134 (1.961 g, 65.6% yield) as an orange solid: 1H NMR (400 MHz, DMSO-d6) delta ppm 8.55 (1 H, s), 8.27 (1 H, d, J=5.9 Hz), 7.95 (1 H, d, J=4.0 Hz), 6.89 – 7.04 (4 H, m), 6.75 (1 H, d, J=3.7 Hz), 3.92 (3 H, s); Mass Spectrum (ESI) m/e = 319.0 [M+l (79Br)] and 321.0 [M+l (81Br)].

393553-57-6, 393553-57-6 6-Bromo-4-methoxy-1H-indole 24728034, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; AMGEN INC.; WO2009/158011; (2009); 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

6958-37-8,6958-37-8, 5-Nitro-1H-indole-3-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-nitroindole-3-carboxylic acid (2.45 g, 12 mmol) in methanol (50 cm3) was added sulphuric acid (1 cm3) and the solution stirred at reflux for 6 hours. The solution was allowed to cool and then poured onto ice-water, neutralised with sodium bicarbonate and the product filtered to give a yellow solid, which was recrystallised from methanol as an off-white solid. Yield 1.76 g, 67%. mp 282-2840C. deltaH 3.85 (3H, s, OCH3), 7.65 (IH, d, J 9, H7), 8.08 (IH, dd, Ji 9, J2 2.3, H6), 8.35 (IH, s, H2), 8.83 (IH, d, J 2.3, H4), 8.5 (IH, s, NH). uv lambdamax/nm 320 (15000), 251 (32450), lambdamin/nm 284, 213; pH 12 lambdamax/nm 366 (13100), 271 (31500), 213 (48100). m/z 243.1 (M+Na)+. Accurate mass measurement on (M+Na)+ Ci0H8N2O4Na 243.0396, deviation -5.73 ppm.

6958-37-8 5-Nitro-1H-indole-3-carboxylic acid 248136, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; MEDICAL RESEARCH COUNCIL; WO2007/135380; (2007); 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