Day: March 11, 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.171879-99-5,4-Chloro-6-methyl-7-azaindole,as a common compound, the synthetic route is as follows.

To a solution of 4-chloro-6-methyl-lH-pyrrolo[2,3-]pyridine (0.5 g, 3 mmol) in MeCN (15 mL) was added 2,6-difluorobenzylamine (2 eq) and pTSA.H20 (2 eq) under N2 at room temperature. The reaction mixture was heated at 150 C in a CEM microwave reactor for 4 hours. The mixture was diluted with sat. aq. NaHC03 (20 mL) solution and EtOAc (20 mL). The organic layer was separated, washed with brine, dried over MgSC^ and concentrated in vacuo. The residue was purified via flash chromatography using MeOH and DCM as eluent to give the product (0.521 g, 1.90 mmol, 63%) as yellow solid. 1H NMR (399 MHz, DMSO-d6) delta 10.96 (s, 1H), 7.43 (tt, 1H), 7.20 – 7.08 (m, 2H), 6.95 (d, 1H), 6.77 (t, 1H), 6.53 (d, 1H), 6.15 (s, 1H), 4.44 (d, 2H), 2.35 (s, 3H)., 171879-99-5

171879-99-5 4-Chloro-6-methyl-7-azaindole 24729584, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; LES LABORATOIRES SERVIER; VERNALIS (R&D) LIMITED; FIUMANA, Andrea; FOLOPPE, Nicolas; RAY, Stuart; WALMSLEY, David; KOTSCHY, Andras; BURBRIDGE, Michael, Frank; CRUZALEGUI, Francisco, Humberto; (141 pag.)WO2017/55533; (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

16732-69-7, Ethyl 7-bromo-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The mixture of ethyl 7-bromo-1H-indole-2-carboxylate (536 mg, 2 mmol), (4- fluorophenyl)boronic acid (420 mg, 3 mmol) in a mixture of toluene, ethanol and sat. NaHCO3 solution (10/4/4 mL) was degassed and Pd(PPh3)4 (100 mg, 0.09 mmol) was added. The reaction mixture was heated at 100 oC overnight and extracted with EtOAc, then washed with brine and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to give the desired product (320 mg, 57% yield) as an off-white powder. 1H NMR (300 MHz, CDCl3) delta 8.89 (br, 1H), 7.69 (d, J = 8.4 Hz, 1H), 7.60 (m, 1H), 7.58 (m, 1H), 7.23 (m, 5H), 4.40 (q, J = 6.9 Hz, 2H), 1.41 (t, J = 6.9 Hz, 3H).

16732-69-7, As the paragraph descriping shows that 16732-69-7 is playing an increasingly important role.

Reference：
Patent; LAVOIE, Edmond J.; PARHI, Ajit; YUAN, Yi; ZHANG, Yongzheng; SUN, Yangsheng; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; TAXIS PHARMACEUTICALS, INC.; (251 pag.)WO2018/165611; (2018); 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.900514-08-1,5-Chloro-3-iodo-7-azaindole,as a common compound, the synthetic route is as follows.

900514-08-1, Step 2: Preparation of 5-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (1.25 g, 4.5 mmol) was dissolved in dry tetrahydrofuran (26 mL), and 60% sodium hydride (270 mg, 6.75 mmol) was added in batches under an ice bath and under a nitrogen atmosphere. The reaction solution was stirred for 15 min under a liquid ice bath, then chlorotriisopropylsilane (1.25 mL, 5.9 mmol) was added dropwise. The reaction solution was warmed to room temperature, then stirred for 2 hrs, quenched with a saturated ammonium chloride aqueous solution, and extracted with ethyl acetate. The organic phase was dried, concentrated and then separated by column chromatography [eluent: petroleum ether] to obtain 5-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.75 g, yield 90%).

As the paragraph descriping shows that 900514-08-1 is playing an increasingly important role.

Reference：
Patent; Abbisko Therapeutics Co., Ltd.; ZHANG, Mingming; ZHAO, Baowei; YU, Hongping; CHEN, Zhui; XU, Yaochang; (58 pag.)US2020/140431; (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

879-37-8,879-37-8, Indole-3-acetamide is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To compound C, indole-3-acetamide (104.71 g) and THF (1428 mL) were added at about 15 C. to about 35 C. under a nitrogen atmosphere. The resulting solution was added dropwise in the range of about 20 C. to about 32 C. over about 30 minutes or longer under a nitrogen atmosphere to a 1 M solution of potassium tert-butoxide in THF (1382.5 mL) further diluted with THF (420 mL). The reaction solution was stirred at about 20 C. to about 32 C. for about 2 hours. Then, 12 M hydrochloric acid (312 mL) was added dropwise at about 50 C. or lower, and the mixture was stirred at about 40 C. to about 50 C. for about 1 hour. After the completion of reaction, water (465 mL) and 28% ammonia water (465 mL) were added to the reaction solution, and the mixture was stirred at about 20 C. to about 32 C. for about 30 minutes or longer and then separated into aqueous and organic layers. The aqueous layer was removed. The organic layers containing compound B were combined and concentrated to about 2100 mL under a reduced pressure at an internal temperature of about 60 C. or lower. Ethanol (4095 mL) was added to the concentrated solution containing compound B. The resulting solution containing compound B was further concentrated to about 2100 mL under a reduced pressure at about 60 C. or lower, and then, ethanol (1050 mL) was added. The solution was concentrated to about 2100 mL under a reduced pressure at about 60 C. or lower to adjust the THF concentration to 2% or less. The concentrated solution obtained was cooled to about 20 C. to about 30 C., and water (2100 mL) was added dropwise over about 1 hour or longer. The resulting mixture containing compound B was stirred at about 20 C. to about 30 C. for 1 hour. The deposited crystals of compound B were collected by filtration and washed with a 50% aqueous ethanol solution (1050 mL). The crystals of compound B were dried in vacuum at about 45 C. to about 55 C. for about 12 hours or longer (178.7 g, yield: 80.9% (calculated based on indole-3-acetamide)). The crystals of compound B thus obtained can be used directly in next step. The crystals of compound B may be further purified as follows: methylene chloride (750 mL) was added to the crystals of compound B (150.0 g), and the mixture was stirred at about 15 C. to about 25 C. for about 2 hours or longer. To this suspension containing compound B, heptane (750 mL) was added dropwise at about 15 C. to about 25 C. over about 1 hour or longer, and the mixture was stirred at about 15 C. to about 25 C. for about 2 hours or longer. The deposited crystals of compound B were collected by filtration and washed with a mixed solvent of methylene chloride and heptane (mixing ratio: 1/1) (450 mL). The crystals of compound B were dried in vacuum at about 45 C. to about 55 C. for about 12 hours or longer (146.1 g, yield from crystals before purification: 97.4%).

The synthetic route of 879-37-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ARQULE, INC.; Nakamura, Yoshitaka; Ooyama, Jo; US2013/281699; (2013); 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.14618-45-2,3-(Trifluoroacetyl)indole,as a common compound, the synthetic route is as follows.

To a solution of 2,2,2-trifluoro-l-(lH-indol-3-yl)ethanone (0.20 g, 0.938 mmol) in THF (1 mL) in an ice-bath was added sodium borohydride (71.00 mg, 1.877 mmol) under N2. Then boron trifluoride diethyl ether (0.357 mL, 2.815 mmol) was added dropwise. The reaction was let stirred for 2 h while warmed to room temperature. The mixture was poured into a mixture of ice-water and 5% aqueous NaHC03and extracted with ethyl acetate. The combined organics were concentrated. The residue was purified by silica gel column chromatography to give the title compound (90 mg). LCMS m/z = 200.4 [M+H]+; NMR (400 MHz, CD3OD) delta ppm 3.57 (q, J = 11.1 Hz, 2H), 7.04 (t, J = 7.4 Hz, 1H), 7.12 (t, J = 7.3 Hz, 1H), 7.20 (s, 1H), 7.37 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 7.9 Hz, 1H).

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; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (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