Day: March 24, 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1065181-58-9,Ethyl 5-bromo-1H-indole-7-carboxylate,as a common compound, the synthetic route is as follows.

Intermediate 104:Ethyl 5-bromo-3-(tetrahydro-3-thienylmethyl)-1 H-indole-7-carboxylate.To a solution of tetrahydro-3-thiophenecarbaldehyde (5.0 g, 43.10 mmol) in dichloromethane (200 mL) was added TMS-OTf (15.4 mL, 86.26 mmol) and ethyl 5- bromo-1 H-indole-7-carboxylate (11.5 g, 43.10 mmol) dropwise at 0 0C. The mixture was stirred at 0 0C for 2h, and then triethylsilane was added at the same temperature, which was maintained for 2h. The reaction was warmed to 20 0C and stirred for 16h. Water was added, the layers were separated, and the organic layer was (Na2SO4),concentrated, and purified on silica gel (PE:EA = 50:1 ), giving 9g (56.4) of the title compound. 1H NMR (CDCI3): delta 1.43 (t, 3H), 2.08 (m, 1 H), 2.58 (m, 2H), 2.88 (m, 6H), 4.44 (q, 2H), 7.09 (s, 1 H), 7.89 (s, 1 H), 7.95 (s, 1 H), 9.65 (s, 1 H).

1065181-58-9, As the paragraph descriping shows that 1065181-58-9 is playing an increasingly important role.

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/118724; (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.923197-75-5,(6-Bromo-1H-indol-2-yl)methanol,as a common compound, the synthetic route is as follows.,923197-75-5

(6-Bromo-1H-indol-2-yl)methanol (80 mg, 0.35 mmol) and dess-martin periodinane (178 mg, 0.42 mmol) were dissolved in dichloromethane (10 mL), and it was stirred for 30 minutes at room temperature. The reaction mixture was diluted with ethyl acetate, and it was washed with 10% sodium thiosulfate, saturated NaHC03and brine. The organic layer was dried over Na2S04, and it was concentrated under reduced pressure. The residue was purified on an ISCO chromatograph (0-10% ethyl acetate/hexane) to give product as a white solid (78 mg, 100%);1H NMR (300 MHz) (CDCb) d 9.86 (s, 1H), 9.23 (bs, 1H), 7.65 (s, 1H), 7.61 (d, J= 9 Hz, 1H), 7.29 (d, j= 9 Hz, 1H), 7.26-7.25 (m, 1H).

923197-75-5 (6-Bromo-1H-indol-2-yl)methanol 13567957, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; TAXIS PHARMACEUTICALS, INC.; LAVOIE, Edmond, J.; SAGONG, Hye Yeon; PARHI, Ajit, K.; (144 pag.)WO2019/99402; (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.1082040-57-0,Methyl 6-chloro-1H-indole-4-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of methyl 6-chloro-1H-indole-4-carboxylate (1000 mg, 4.77 mmol) in tetrahydrofuran (20 mL) was added allyl alcohol (0.324 mL, 4.77 mmol), and the mixture was degassed for 5 minutes by bubbling nitrogen. Triethylborane (1.431 mL, 1.431 mmol) and tetrakis(triphenylphosphine)palladium(0) (276 mg, 0.239 mmol) were added and the mixture was heated to 75 C and stirred at 75 C for 18 hours. The mixture was concentrated and the residue was purified using column chromatography (silica gel, 0 to 70% EtOAc in hexanes) to afford methyl 3-allyl-6-chloro-lH-indole-4-carboxylate (714 mg, 60%) as a white solid. LC-MS(ES) m/z = 250 [M+H]+., 1082040-57-0

1082040-57-0 Methyl 6-chloro-1H-indole-4-carboxylate 53399422, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; MILLER, William Henry; ROMERIL, Stuart Paul; VERMA, Sharad Kumar; TIAN, Xinrong; WO2015/132765; (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

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

In 50ml absolute diethyl ether 5g 2,2,2-trifluoro-1-(1H-indol-3-yl)-ethanone are dissolved. 15.6ml of a methyl magnesium bromide solution (3 molar, in diethyl ether) is added slowly while the reaction temperature is kept at -10C. The mixture is allowed to warm up to 20C and is stirred for 2 hours. The reaction mixture is then treated with saturated ammonium chloride solution and the organic layer separated. The aqueous phase is extracted with diethyl ether and the combined organic phases dried over magnesium sulfate. The organic phase is evaporated in vacuo to give 1,1,1-trifluoro-2-(1H-indol-3-yl)-propan-2-ol, which is used without further purification.

14618-45-2, 14618-45-2 3-(Trifluoroacetyl)indole 589126, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Novartis AG; EP1783114; (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

525593-33-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.525593-33-3,3-Bromo-5-nitroindole,as a common compound, the synthetic route is as follows.

General procedure: A mixture of 5-nitro-1H-indole (200mg, 1.23mmol) or its derivatives and dry DMF (5mL) was cooled to 0C and NaH (60mg, 1.23mmol) was added. After the addition, the reaction mixture was stirred at r.t. for 0.5-1h, then compound 4 (282mg, 1.23mmol) was added, and the reaction mixture was allowed to stirred for an additional 2h. After a sequence of extraction, wash, and concentration, the crude product compound 5 (222mg, 0.72mmol, 58.30%) was obtained and could be used in next step without further purifications [12].

As the paragraph descriping shows that 525593-33-3 is playing an increasingly important role.

Reference：
Article; Wu, Zeng; Yan, Ming; Hu, Shi-He; Yu, Zhi-Cheng; Zhu, Yong; Cheng, Ya-Dong; Liu, Hai-Chun; Zhang, Yan-Min; Yao, Si-Hui; Tang, Wei-Fang; Lu, Tao; Chinese Chemical Letters; vol. 25; 2; (2014); p. 351 – 354;,
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.879-37-8,Indole-3-acetamide,as a common compound, the synthetic route is as follows.,879-37-8

Step 6 To a solution of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl) oxoacetic acid methyl ester (1.0 g, 4.12 mmol) and indole-3-acetamide (0.8 g, 4.5 mmol) in anhydrous tetrahydrofuran at 0 C. was added a solution of potassium t-butoxide (1M in tetrahydrofuran) (12.4 mL, 12.4 mmol) dropwise over 30 minutes. The mixture was stirred at 0 C. for 2 hours. Concentrated hydrochloric acid (10 mL) was then added and the mixture stirred for 1 hour at room temperature. The mixture was then diluted with ethyl acetate (200 mL), washed twice with water (50 mL), and saturated aqueous sodium chloride solution (50 mL) and the organic layer dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography, eluting with ethyl acetate/hexanes (1:4) to afford 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl) pyrrole-2,5-dione as a bright red solid (1.2 g, 80%). 1H NMR (CDCl3) 400 MHz delta: 8.5 (brs, 1H), 7.78 (s, 1H), 7.63 (d, 1H, J=2.8 Hz), 7.44 (s, 1H), 7.35 (d, 1H, J=8 Hz), 7.16 (d, 1H, J=8.4 Hz), 7.11 (t, 1H, J=7.6 Hz), 6.86 (t, 1H, J=7.6 Hz), 6.80 (d, 1H, J=7.2 Hz), 6.64 (t, 1H, J=8 Hz), 6.57 (d, 1H, J=8 Hz), 4.2 (t, 2H, J=6 Hz), 2.96 (t, 2H, J=6 Hz), 2.24 (m, 2H).

879-37-8 Indole-3-acetamide 397, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; ArQule, Inc.; Kyowa Hakko Kirin Co., Ltd.; Chan, Thomas C.K.; France, Dennis S.; Ishii, Kenichi; Pucci, Paolo; (69 pag.)US2015/328208; (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

900514-08-1,900514-08-1, 5-Chloro-3-iodo-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Preparation of 5-Chloro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (40)5-Chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (39, 31.2 g, 0.112 mmol) was dissolved in N-methylpyrolidinone (800 mL) and NaH (60% dispersion, 4.93 g, 0.123 mol) was added at room temperature. The resulting mixture was stirred for 30 minutes. To this mixture was then added triisopropylsilylchloride (24.0 mL, 0.112 mol) and the resulting mixture was stirred for 2 hours. The reaction was quenched with water and extracted with ethyl acetate three times, washed by brine, dried, filtered, and concentrated in vacuo. The residue was subjected to silica gel flash chromatography (eluted by heptane to 5% ethyl acetate/heptane) to afford the desired compound (43 g, 88%) as a pale-yellow solid

The synthetic route of 900514-08-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Spevak, Wayne; Cho, Hanna; Ibrahim, Prabha N.; Shi, Shenghua; Mamo, Shumeye; Gillette, Samuel J.; Zhu, Hongyao; US2008/167338; (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.640735-23-5,4-Fluoro-7-azaindole,as a common compound, the synthetic route is as follows.,640735-23-5

Example 44 2-(2, 3-DIFLUORO-PHENYL)-1-(4-FLUORO-LH-PYRROLO [2S3-B] PY ridin-3-yl)-ethanone [0256] 4-FLUORO-LH-PYRROLO [2, 3-B] PYRIDINE (230mg, 1. 69MMOL) (ORG. Lett. 2003,5 (26), 5023) and AlCl3 (678, 5. lmmol) in methylene chloride (30mL) were stirred for 0.5hr. To this mixture was added 2,3-Difluoro-phenyl)-acetyl chloride (644mg, 3. 38MMOL) and the reaction solution was stirred for 14HR. Quenched with methanol (50mL) and water (50mL) and extracted with ethyl acetate, dried (NA2SO4). Flash chromatography (methylene chloride/methanol) afforded 2- (2, 3-Difluoro-phenyl)-l- (4-fluoro-lH-pyrrolo [2, 3-B] PY ridin-3-yl)-ethanone (448mg, 91% YIELD). LC/MS : RT 3.16mins. ; m/e 287.1 (M+H), 285.2 (M-H).

As the paragraph descriping shows that 640735-23-5 is playing an increasingly important role.

Reference：
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2005/28475; (2005); 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

170147-29-2, tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a 250 mL flask was placed tert-butyl 5-(BENZYLOXY)-1H-INDOLE-1-CARBOXYLATE (3.3 g, 14 MMOL) in 100 mL of acetone. 1,3-Dibromopropane (5.74 mL, 56.6 MMOL) was added, followed by cesium carbonate (5.5 g, 17 MMOL). The reaction was heated to reflux for 5 h. The reaction was cooled to room temperature and diluted with water (200 mL). The mixture was transferred to a separatory funnel and extracted with ethyl acetate (2 x 150 mL). The combined organics were dried (MGS04), filtered, and evaporated. The residue was then purified via flash chromatography to provide 4.7 g of TERT-BUTYL 5- (3- BROMOPROPOXY)-1H-INDOLE-1-CARBOXYLATE (94%). 1H-NMR (DMSO-D6) No. 7.99-7. 89 (d, 1H), 7.61 (s, 1H), 7.17 (s, 1H), 6.98-6. 91 (d, 1H), 6.62 (s, 1H), 4.16-4. 05 (t, 2H), 3.64 (t, 2H), 2.37-2. 20 (m, 2H). LCMS RT= 3.55 min; [M] += 254. 1., 170147-29-2

The synthetic route of 170147-29-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2004/43950; (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.5192-03-0,1H-Indol-5-amine,as a common compound, the synthetic route is as follows.

Glacial acetic acid (1.3 mL, 22.7 mmol) and sodium triacetoxyborohydride (6.73 g, 31.7 mmol) were added to a solution of 5-aminoindole (3 g, 22.7 mmol), 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (4.52 g, 22.7 mmol) in 1,2-dichloroethane (100 mL). The reaction mixture was stirred for 4 hours at room temperature; an aqueous solution of NaOH (1 M, 100 mL) was then added. The organic layer was separated, dried over MgSO4, filtered and evaporated under reduced pressure to give 6.9 g (96% yield) of 4-(1H-indol-5-ylamino)-piperidine-1-carboxylic acid tert-butyl ester as a black foam; this material was used without further purifications for the next step., 5192-03-0

5192-03-0 1H-Indol-5-amine 78867, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Iyer, Pravin; Lucas, Matthew C.; Schoenfeld, Ryan Craig; Weikert, Robert James; US2009/247568; (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