Day: March 17, 2022

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.61019-05-4,5-Methoxy-7-methyl-1H-indole,as a common compound, the synthetic route is as follows.

61019-05-4, Oxalyl chloride (0.17 mL, 1.93 mmol) was added dropwise via syringe over 1 min to DMF (1.5 mL) in a vial charged with a magnetic stir bar under N2 at 0 C. After ~30 min, 5-methoxy-7-methyl-1H-indole (342 mg, 2.123 mmol) was added dropwise via syringe over ~30 s as a solution in DMF (2 mL). The reaction was allowed to warm to room temperature and stir overnight, after which 1 N NaOH (2 mL) was added dropwise via syringe over 30 s. The reaction was then heated to 100 oC for 20 min, after which it was cooled to room temperature. After 28 h of total reaction time, the mixture was diluted with H2O (15 mL) and DCM (20 mL). The organic layer was separated, and the aqueous layer was washed with DCM (10 mL). The combined organic layers were washed with H2O (2 × 15 mL) and brine (10 mL), dried with Na2SO4, filtered, and concentrated in vacuo to provide a dark red crude residue. The crude material was purified via flash chromatography on silica (24 g column, 0-60% EtOAc/heptane) to afford 300 mg (82% yield) of 13 as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 12.27 – 11.84 (m, 1H), 9.89 (s, 1H), 8.20 (d, J = 3.30 Hz, 1H), 7.41 (d, J = 2.45 Hz, 1 H), 6.71 (dd, J = 2.32, 0.73 Hz, 1H), 3.76 (s, 3H), 2.48 – 2.43 (m, 3H); LCMS m/z = 190.2 ([M+H]+), tR = 1.00 min (method A).

The synthetic route of 61019-05-4 has been constantly updated, and we look forward to future research findings.

Reference：
Article; DeChristopher, Brian; Park, Soo-Hee; Vong, Linh; Bamford, Derek; Cho, Hyun-Hee; Duvadie, Rohit; Fedolak, Allison; Hogan, Christopher; Honda, Toshiyuki; Pandey, Pramod; Rozhitskaya, Olga; Su, Liansheng; Tomlinson, Elizabeth; Wallace, Iain; Bioorganic and Medicinal Chemistry Letters; vol. 29; 8; (2019); p. 991 – 994;,
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

2 g of intermediate I-1 and 6 g of ethoxycarbonyl methylene triphenylphosphine are dissolved in 50 ml of dry acetonitrile.70 overnight.TLC showed complete conversion of the substrate.Stop the reaction,The reaction was cooled to room temperature.Add 50ml ethyl acetate and 50ml water,Extraction and separation of water layer,The organic layer is dry,concentrate,Column chromatography gave 6.1 g of intermediate I-17 (white solid, yield 85%).

2795-41-7, 2795-41-7 6-Fluoroindole-3-carboxaldehyde 262903, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Hu Youhong; Geng Meiyu; Xing Weiqiang; Ding Jian; Ai Jing; (86 pag.)CN103664895; (2018); B;,
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.39689-58-2,2-(1H-Indol-6-yl)acetic acid,as a common compound, the synthetic route is as follows.

Hydroxybenzotriazole (614 mg, 4.5 mmol), 4-ethylmorpholine (320 mul, 2.5 mmol), propargylamine (160 mul, 2.5 mmol) and 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (523 mg, 2.7 mmol) were added to an ice cold solution of (1H-indol-6-yl)-acetic acid (640 mg, 2.2 mmol; U.S. Pat. No. 4,894,386 A) in tetrahydrofuran (6.4 ml). The solution was naturally warmed to ambient temperature and stirred for 14 h. Ice water/brine 1/1 was added and the mixture was extracted two times with dichloromethane. The combined extracts were successively washed with 1 N HCl, brine, 1 N NaOH and brine, and dried over sodium sulfate. The solvent was removed under reduced pressure to give brown crystals which were recrystallized from heptane/dichloromethane to give 380 mg (1.8 mmol, 80%) of the title compound as colorless crystals. MS: 213.4 (M+H)+., 39689-58-2

39689-58-2 2-(1H-Indol-6-yl)acetic acid 14882503, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Ackermann, Jean; Aebi, Johannes; Binggeli, Alfred; Grether, Uwe; Kuhn, Bernd; Maerki, Hans-Peter; Meyer, Markus; US2006/35956; (2006); 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.219552-64-4,tert-Butyl 6-nitro-1H-indole-1-carboxylate,as a common compound, the synthetic route is as follows.

Step 2.Synthesis of 6-Amino-2,3-dihdro-indole-1-carboxylic acid t-butyl ester 6-Nitro-indole-1-carboxylic acid t-butyl ester (1 eq) was dissolved in methanol (0.1M), to this solution was added palladium on carbon (0.1 eq) in methanol under nitrogen.A hydrogen atmosphere was then inserted and resulting mixture allowed to stir for 3 hours at room temperature.The reaction mixture was then filtered through celite and solvent removed in vacuo to afford 6-Amino-2,3-dihdro-indole-1-carboxylic acid t-butyl ester as a white solid. MS: MH+235, 219552-64-4

219552-64-4 tert-Butyl 6-nitro-1H-indole-1-carboxylate 22240526, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Amiri, Payman; Fantl, Wendy; Levine, Barry Haskell; Poon, Daniel J.; Ramurthy, Savithri; Renhowe, Paul A.; Subramanian, Sharadha; Sung, Leonard; US2004/122237; (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

399-67-7, 7-Fluoro-1H-indole-2-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 7-fluoro-1H-indole-2-carboxylic acid (78 mg, 0.435 mmol), (5)- 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5 -(piperidin-3 -yl)benzofuran-3 – carboxamide (100 mg, 0.2 18 mmol) in DCM (1 ml) was added N,N-diisopropylethylamine (169mg, 1.306 mmol), and the reaction mixture stirred for 5 mm at RT. Then 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (415 mg, 0.653 mmol) was added to the reaction mixture and stirred at RT overnight under N2 protection. The reaction mixture was concentrated under vacuum, then applied onto a silica gel column and eluted with 0-30% MeOH/EtOAc. This resulted in 78 mg (58%) of (S)-5-( 1 -(7-fluoro- 1 H-indole-2-carbonyl)piperidin-3 -yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3 -carboxamide as white solid. LC-MS (ES, mlz) C32H30F2N4055: 620; Found: 621 [M+H].

399-67-7, As the paragraph descriping shows that 399-67-7 is playing an increasingly important role.

Reference：
Patent; MERCK SHARP & DOHME CORP.; HE, Shuwen; LAI, Zhong; DAI, Xing; XIAO, Dong; LONDON, Clare; ZORN, Nicolas; NARGUND, Ravi; PALANI, Anandan; MCCOMAS, Casey, C.; LI, Peng; PENG, Xuanjia; SOLL, Richard; WO2014/209729; (2014); 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

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

General procedure: To a stirred solution of 25 (115 mg, 0.5 mmol) in DCM (10 mL) was added carboxylic acid (0.5 mmol), HOBT (68 mg, 0.5 mmol) and EDCI·HCl (144 mg, 0.75 mmol). The mixture was stirred at room temperature overnight, and washed successively with water (5 mL) and brine (10 mL × 2). The organic layer was dried over anhydrous Na2SO4, and concentrated to give the crude product, which was purified by flash chromatography (hexane/EtOAc = 3:1-1:1) afforded 4a-w.

90924-06-4 1-Methyl-4-indolecarboxylic Acid 14987287, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Xia, Guangxin; You, Xiaodi; Liu, Lin; Liu, Haiyan; Wang, Jianfa; Shi, Yufang; Li, Ping; Xiong, Bing; Liu, Xuejun; Shen, Jingkang; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 1 – 10;,
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.6127-19-1,6-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