Category: indole-building-block

53462-88-7, Methyl 3-formyl-1H-indole-4-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

53462-88-7, A) 2.1 g of 80% pure sodium hydride were added in portions to a solution of 7 g of methyl 3-formylindole-4-carboxylate (see Example 1A for preparation) in 250 ml of dry dimethylformamide at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at 50 C. for 1 hour. Subsequently, 7 ml of methyl iodide was added through a dropping funnel, and the reaction mixture was stirred at 50 C. for a further 2 hours. To work up the reaction mixture it was evaporated to dryness under reduced pressure and taken up in a mixture of 50 ml of water and 50 ml of dichloromethane. The dichloromethane phase was separated, and the aqueous phase was extracted once more with 50 ml of dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered and evaporated. The remaining crystalline crude product was recrystallized from diethyl ether. Drying of the crystals resulted in 6.9 g of methyl 1-methyl-3-formylindole-4-carboxylate with a melting point of 128-129 C.

The synthetic route of 53462-88-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Kali-Chemie Pharma GmbH; US5272143; (1993); A;,
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

640735-23-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.640735-23-5,4-Fluoro-7-azaindole,as a common compound, the synthetic route is as follows.

[0723] To a stirred solution of 4-fluoro-1H-pyrrolo [2,3-bj pyridine (1.4 g, 10 mmol) in DMF (42 mL) at 0 C under an argon atmosphere were added potassium carbonate (2.1 g, 15 mmol) and methyl iodide (1.75 g, 12 mmol). The reaction mixture was warmed to room temperature and stirred for 12 h. After consumption of starting material (by TLC), the reaction mixture was diluted with water (100 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 15%EtOAc:Hexane to afford 4-fluoro-1-methyl-1H-pyrrolo [2,3-bj pyridine (700 mg, 45%) as pale brown liquid. ?H NMR (CDC13, 400 MHz): 8.26 (dd, 1H), 7.12 (d, 1H), 6.78 (dd, 1H), 6.51 (d, 1H), 3.90 (s, 3H); TLC: 20% EtOAc Hexane (Rj: 0.5).

The synthetic route of 640735-23-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (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

192189-07-4, tert-Butyl 3-iodo-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,192189-07-4

In a 100 mL round bottom flask, N-Boc-3-iodoindole (0.65 g, 1.45 mmol),Tetrakis (triphenylphosphine) palladium (0.1g, 0.04mmol) was dissolved in 10mL of 1,4-dioxane,Replace gas. Triethylamine (2 mL, 14.5 mmol) and pinacol borane (0.3 mL, 2.2 mmol) were added with a syringe, and the mixture was stirred at 80 C after the dropwise addition. Stop heating after 3h,After cooling to room temperature, Ia-1 (0.58 g, 1.45 mmol) was added to the system under the protection of argon.Cesium carbonate (2.4 g, 7.25 mmol), 12 mL of methanol. After the addition was complete, the system was stirred at 100 C. overnight and monitored by TLC. After the reaction is completed, spin column chromatography is directly performed (V dichloromethane: V methanol = 100: 1 ? V dichloromethane: V methanol = 20: 1),The crude product was directly dissolved in 20 mL of acetonitrile, Boc2O (0.62 mL, 2.7 mmol) was added thereto, DMAP (0.1 g, 0.3 mmol) was stirred at room temperature for 2 h, and TLC was monitored.After the reaction was completed, spin column chromatography was performed directly (V petroleum ether: V ethyl acetate = 100: 1 ? V petroleum ether alkane: V ethyl acetate = 10: 1) to obtain 0.2 g of a white solid with a yield of 30%.

The synthetic route of 192189-07-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Nankai University; Wang Qingmin; Liu Yuxiu; Dong Ji; Wang Ziwen; Song Hongjian; Li Yongqiang; (22 pag.)CN110759893; (2020); A;,
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 solution of this compound (11 g, 50 mmol) in 100 mL acetone were added MeI (10 mL, 150 mmol) and potassium carbonate (18 g), and stirring was continued at RT for 2 h. Acetone was removed in vacuo. Water and methylene chloride were added to the residue. The organic layer was separated, washed with brine, dried and concentrated in vacuo to yield crude 1-methyl-3-trifluoroacetyl-1H-indole., 14618-45-2

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

Reference：
Patent; Monsanto Company; US5994270; (1999); A;,
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

162100-95-0, 6-Fluoro-5-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 6-fluoro-5-methyl-1 H-indole [CAS 162100-95-0] (1.7 g, 11 .4 mmol) in CH2CI2 (100 mL) was cooled to 0C under N2-atmosphere. A solution of diethylaluminum chloride 1M in hexane (17.1 mL, 17.1 mmol) was added dropwise and the resulting mixture was kept at 0C for 15 mm. A solution of 2-(4-chloro-2-methoxyphenyl)acetyl chloride 9a? (3.50 g, 16 mmol) in CH2CI2 (50 mL) was added dropwise. Stirring was continued at 0C for 1 h and the reaction mixture was subsequently stirred at room temperature for 2 h. The reaction mixture was poured out into a stirring ice/Rochelle salt solution. After the ice had melted, the mixture was filtered over dicalite and the filter cake was washed several times with THE.The filtrates were combined. The layers were separated and the organic layer was washed with brine, dried over Mg504, filtered and evaporated under reduced pressure. The solid residue was suspended in CH2CI2 (30 mL) and the precipitate was filtered off and dried under vacuum at 500C to provide 2-(4-chloro-2- methoxyphenyl)-1 -(6-fluoro-5-methyl-1 H-indol-3-yl)ethanone 9a (2.76 g)., 162100-95-0

The synthetic route of 162100-95-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; COESEMANS, Erwin; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (96 pag.)WO2017/167952; (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

39689-58-2, 2-(1H-Indol-6-yl)acetic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

h. N-Cyclopentylmethylindole-6-acetamide A solution of indole-6-acetic acid (0.70 g) and 1,1′-carbonyldiimidazole (0.83 g) in methylene chloride (20 ml) and N,N-dimethylformamide (5 ml) was heated at reflux for 20 min, treated with cyclopentylmethylamine (0.59 g), and heated at reflux for an additional 3 hr. The solution was diluted with methylene chloride; washed successively with 10% v/v hydrochloric acid, water and brine; dried (MgSO4); and evaporated. The residue was purified by flash chromatography, eluding with 1:19 ethyl acetate: hexane, to give N-cyclopentylmethylindole-6-acetamide (0.83, 81%) as a white powder; partial NMR (80 MHz, CDCl3): 3.13(t, 2H, NHCH2), 3.69(s, 2H, ArCH2), 6.55(m, 1H, H3 -indole), 6.98(dd, 1H, H5 -indole), 7.62(d, 1H, H4 -indole)., 39689-58-2

As the paragraph descriping shows that 39689-58-2 is playing an increasingly important role.

Reference：
Patent; ICI Americas Inc.; US4894386; (1990); A;,
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

10075-48-6, 5-Bromo-3-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

10075-48-6, Step B 5-Bromo-1,3-dimethylindole To a stirred solution of 5-bromo-3-methylindole (2.85 g., 13.6 mmol., 1 eq.) in DMF (35 mL.) was added NaH (651 mg. of a 60% dispersion in oil, 16.28 mmol., 1.2 eq.). The mixture was stirred 15 minutes. To this mixture was added iodomethane (0.930 mL., 14.93 mmol., 1.1 eq.). The mixture was stirred for 2 hours. The DMF was removed in vacuo. The residue was diluted with water and extracted 4* with Et2 O. The organic extracts were combined, dried over anhydrous MgSO4, filtered and concentrated in vacuo giving 3.04 g. 5-bromo-1,3-dimethylindole as a reddish liquid.

10075-48-6 5-Bromo-3-methyl-1H-indole 254707, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Merck & Co., Inc.; US5252732; (1993); A;,
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.227960-12-5,Methyl 5-methylindole-3-carboxylate,as a common compound, the synthetic route is as follows.

Methyl 5-methyl-1H-indole-3-carboxylate (200 mg, 1.06 mmol) used hydrolysis reaction (2 NNaOH water solution) to aord DX-01-03 (white solid, 150 mg, yield 81%). 1H-NMR (400 MHz,CD3OD): = 8.15 (d, J = 1.8 Hz, 1H, H-indolyl), 8.07 (s, 1H, H-indolyl), 7.39 (d, J = 8.3 Hz, 1H,H-indolyl), 7.15 (dd, J = 8.3, 1.1 Hz, 1H, H-indolyl), 2.46 (s, 3H, CH3). 13C-NMR (101 MHz, CD3OD): = 137.41, 134.35, 127.80, 127.00, 122.51, 120.09, 117.20, 113.08, 110.78, 21.77. HRMS (ESI): m/z [M + H]+calculated for C10H10NO2: 176.07061; found: 176.07094., 227960-12-5

As the paragraph descriping shows that 227960-12-5 is playing an increasingly important role.

Reference：
Article; Wen, Hui; Liu, Yuke; Wang, Shufang; Wang, Ting; Zhang, Gang; Chen, Xiaoguang; Li, Yan; Cui, Huaqing; Lai, Fangfang; Sheng, Li; Molecules; vol. 24; 11; (2019);,
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

90924-06-4, 1-Methyl-4-indolecarboxylic Acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,90924-06-4

To a solution of 4-METHYL-4- [ (3S)-3-METHYL-4- [ (1 R)-1- [4- (TRIFLUOROMETHYL) PHENYL] ETHYL] PIPERAZIN-1-YL]-1-PIPERIDINECARBOXYLIC ACID-DIMETHYLETHYL ester (127 mg, 0.27 MMOL) in CH2CI2 (3 mL) was added trifluoromethyl acetic acid (1.5 mL) at room temperature. After 2h the reaction mixture was concentrated in vacuo, and dried under vacuum for 3 h. Re-dissolved the product in DMF (5 mL), then 1-methyl-1 H-indol-4-carboxylic acid (52 mg, 0.30 MMOL), Et3N (55 mg, 0.54 MMOL), and HATU (134 mg, 0.35 MMOL) was added successively at room temperature. After 16 h the reaction mixture was poured into ice water (10 mL), and the mixture was extracted with EtOAc (3X20 mL). The organic phase was washed with NAHCO3 (10 mL, sat. ) and brine (10 mL), and dried over NA2SO4. Concentration in vacuo, and purification by column chromatography (CH2CI2-MEOH, 9: 1) afforded the title compound as a yellow solid. MS: 526 (M+).’H NMR (CDCl3, 400MHZ) : S : 0.9 (s, 3H), 1.14 (d, 3H), 1.3 (d, 4H), 1.4-1. 8 (m, 2H), 1.82-2. 05 (m, 1H), 2.18-2. 8 (m, 6H), 2.9-3. 1 (m, 1H), 3.1-3. 3 (m, 1H), 3.3-3. 7 (m, 2H), 3.8 (s, 3H), 3.9-4. 3 (m, 2H), 6.48 (m, 1H), 7.05-7. 16 (m, 2H), 7. 18-7. 28 (M, 1 H), 7.3-7. 38 (m, 1 H), 7.46-7. 6 (m, 4H).

As the paragraph descriping shows that 90924-06-4 is playing an increasingly important role.

Reference：
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (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

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

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%.

2795-41-7, The synthetic route of 2795-41-7 has been constantly updated, and we look forward to future research findings.

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