Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31241-19-7,5-Methoxy-2,3,3-trimethyl-3H-indole,as a common compound, the synthetic route is as follows.,31241-19-7

General procedure: 2,3,3-Trimethylindolenine (1 g, 12.56 mmol), acetonitrile (50 mL),and methyl idodide (0.94 mL, 15.072 mmol) were refluxed at 80 C for 7 h. The resulting pink precipitate was filtered and washed with ice-cooled chloroform. Yield: 37%.

As the paragraph descriping shows that 31241-19-7 is playing an increasingly important role.

Reference：
Article; Kim, Bo Hyung; Park, Se Woong; Lee, Donghyun; Kwon, I. I. Keun; Kim, Jae Pil; Bulletin of the Korean Chemical Society; vol. 35; 8; (2014); p. 2453 – 2459;,
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.90924-06-4,1-Methyl-4-indolecarboxylic Acid,as a common compound, the synthetic route is as follows.

90924-06-4, To a stirred SOLUTION OF 4- [ (Z)- (4-BROMOPHENYL) (ethoxyimino) methyl]-1- (4-methyl-4- piperidinyl) piperidine (50 mg, 0.12 MMOL), 1-METHYL-1 H-indole-4-carboxylic acid (23 mg, 0.13 MMOL), and Et3N (24.3 mg, 0.24 MMOL) in DMF (2 mL), HATU (60.8 mg, 0.16 MMOL) was added at room temperature. After 16 h the mixture was poured into ice water (10 mL), and extracted with CH2CI2 (3X10 mL). The organic phase was dried over NA2SO4, and concentrated in vacuo. Purification by preparative TLC afforded title compound as a light YELLOW OIL. H NMR (CDCl3, 400MHz) 8 0.93 (s, 3H), 1.2 (t, 3H), 1.24-2. 2 (m, 11 H), 2.34-2. 46 (m, 1H), 2.76-2. 9 (m, 1 H), 2.9- 3.1 (m, 1H), 3.1-3. 3 (m, 1 H), 3.3-3. 7 (m, 2H), 3.78-3. 84 (s, 3H), 4.02-4. 18 (q, 2H), 6.4-6. 6 (m, 1H), 7.08-7. 14 (m, 4H), 7.19-7. 25 (m, 1H), 7.32-7. 36 (m, 1H), 7.48-7. 56 (m, 2H).

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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.2795-41-7,6-Fluoroindole-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

General procedure: The van Leusen reaction was conducted as describedpreviously [37]. Aromatic aldehyde (3 mmol) was mixed withamine (15 mmol) in 20 mL of dry methanol. The reaction mixturewas left overnight to complete imine formation, although thisprocess can be monitored by this layer chromatography (TLC) (SiO2/CHCl3). Anhydrous K2CO3 (3 mmol) and TosMIC (tosylmethylisocyanide,3 mmol) were subsequently added. The mixture was stirredfor an additional 8 h, diluted with 50 mL of H2O, and extractedthree times with 20 mL of ethyl acetate. The combined extractswere washed twice with 20 mL of H2O, and once with 20 mL ofbrine, treated with anhydrous magnesium sulfate and evaporated.The final products were purified either by trituration under a 2:1hexane:isopropanol mixture, or chromatography on a short silicagelbed. The unreacted aldehydes were eluted with ethyl acetate orchloroform, and a mixture of AcOEt:MeOH or CHCl3:MeOH wasthen applied to elute the product.

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

Reference：
Article; Hogendorf, Adam S.; Hogendorf, Agata; Popio?ek-Barczyk, Katarzyna; Ciechanowska, Agata; Mika, Joanna; Sata?a, Grzegorz; Walczak, Maria; Latacz, Gniewomir; Handzlik, Jadwiga; Kie?-Kononowicz, Katarzyna; Ponimaskin, Evgeni; Schade, Sophie; Zeug, Andre; Bijata, Monika; Kubicki, Maciej; Kurczab, Rafa?; Lenda, Tomasz; Staro?, Jakub; Bugno, Ryszard; Duszy?ska, Beata; Pilarski, Bogus?aw; Bojarski, Andrzej J.; European Journal of Medicinal Chemistry; vol. 170; (2019); p. 261 – 275;,
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

399-51-9, 6-Fluoro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Trifluoroacetic anhydride (9.009 ml, 64.8 mmol, 2.2 equiv.) was added drop wise to a stirring solution of 6-fluoroindole (4.000 g, 29.6 mmol, 1.0 equiv.) in DMF (25 mL) at 0C (external ice bath temperature). After 3 hours in the ice bath the mixture was quenched with 40 mL of 2N sodium carbonate. The precipitate was collected by filtration and washed with water. The solid was taken up in 4M NaOH (50 mL) and refluxed for 4 hours. The reaction mixture was cooled to room temperature and poured into 50 mL of water. The mixture was cooled in an ice bath and slowly brought to pH 3 with 6N HCl. The precipitate which formed was collected by filtration, washed with water and dried under vacuum to give an off -white solid (3.5 g, 66%). 1H NMR (DMSO-d6, 300 MHz): 12.03 (bs, 1H), 11.87 (s, 1H), 7.99-7.92(m, 2H), 7.23 (dd, J=9.9 & 2.4 Hz, 1Eta),7.03-6.97 (m, 1H)., 399-51-9

The synthetic route of 399-51-9 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BUCK INSTITUTE FOR RESEARCH ON AGING; JOHN, Varghese; BREDESEN, Dale, E.; SPILMAN, Patricia, R.; JAGODZINSKA, Barbara; (85 pag.)WO2017/197177; (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

5192-03-0, 1H-Indol-5-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

DMSO (10 L, 11 kg), 2-amino-3,5-dibromopyrazine (1) (4.5 kg, 17.8 mol, 1 eq.), 5- amino indole (2) (3.06 kg, 23.15 mol, 1.3 eq.) and triethylamine (7.4 L, 5.4 kg, 53.36 mol, 3 eq.) were charged to a reactor. The reaction mixture was heated to 95C while agitated. After 12 hours, the heating was discontinued and the conversion was 88% of 2-amino-3,5-dibromopyrazine. The reaction was heated again to 95C and agitated for an additional 2.5 hours. There was no improvement in conversion. The reaction mixture was agitated at ambient temperature overnight. Triethylamine (3.5 kg) was removed under vacuum and the remaining reaction mixture was transferred to a stainless steel container from which it was charged into another reactor. Subsequently, 8.4 kg of 50% acetic acid (aq.) was introduced over a period of 20 minutes under agitation, followed by purified water (61 L) charged over a period time of 60 minutes. The slurry was then filtered and the isolated material was washed with 2 x 20 L of 1 % acetic acid (aq.). The isolated 3-bromo-N-3-(1H-indol-5-yl)-pyrazine-2,3-diamine) (3) was transferred to a drying cabinet and dried to invariable weight at 40±3C, (19 hours), to afford 4.36 kg, 14.34 mol, 81 % yield, with a purity of 96% by HPLC. The reaction temperature in the batch record was set to be 130-135C. However, at 95C the reaction mixture was at reflux., 5192-03-0

As the paragraph descriping shows that 5192-03-0 is playing an increasingly important role.

Reference：
Patent; AKINION PHARMACEUTICALS AB; LEHMANN, Fredrik; BREMBERG, Ulf; SOeLVER, Ellen; ERIKSSON BAJTNER, Johan; THORNQVIST OLTNER, Viveca; WO2013/89636; (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

101495-18-5, 4,6-Dichloro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step b Ethyl 2,-(hydroxyimino)-3-(4,6-dichloro-3-indolyl)propanoate Mix 4,6-dichloroindole (5.90g, 31.72mmol), potassium carbonate (1.81g, 47.6mmol) and anhydrous methylene chloride (200mL). Stir and add a solution of ethyl 3-bromo-2-hydroxyiminopropanoate (7.00g, 33.31mmol) in methylene chloride (75mL). Stir under a nitrogen atmosphere for 48 hours. Take the solution up in methylene chloride (100mL) and wash with water (300mL), saturated sodium hydrogen carbonate (200mL) and brine (100mL). Dry (MgSO4) and evaporate the solvent in vacuo to give a tan solid. Purify by silica gel chromatography (1 to 3% acetone in chloroform) to give the title compound as a yellow solid (7.00g, 99% based on consumed starting material). Recrystallize (diethyl ether/hexane) to give the tit le compound as white crystals (4.0g, 56%); mp 175-176 C. 1 H NMR (DMSO-d6 /TMS): 1.19 ppm (3H, t), 4.15 ppm (2H, q), 4.15 ppm (2H, s), 6.95 ppm (1H, s), 7.10 ppm (1H, d), 7.40 ppm (1H, d), 11.3 ppm (1H, bs), 12.35 (1H, s)., 101495-18-5

The synthetic route of 101495-18-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Merrell Dow Pharmaceuticals Inc.; US5360814; (1994); 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.162100-95-0,6-Fluoro-5-methyl-1H-indole,as a common compound, the synthetic route is as follows.

Diethylaluminum chloride 1M in hexane (25.1 mL, 25.1 mmol) was addeddropwise, at 000 and under N2-flow, to a solution of 6-fluoro-5-methyl-1 H-indole[CAS 162100-95-0] (2.5 g, 16.8 mmol) in CH2CI2 (135 mL). After 10 mm at 0C, a solution of 2-(2-(2-(benzyloxy)ethoxy)-4-fluorophenyl)acetyl chloride le (8.11 g, 25.1 mmol) in CH2CI2 (50 mL) was added dropwise at 0C over a period of 45 mm, while keeping the reaction temperature below 5C. The reaction was stirred at 0Cfor 2 h and at 10C for 2 h. The reaction mixture was cooled to 0C, and a solution of Rochelle salt [6100-16-9] (9.46 g, 33.5 mmol) in water (10 mL) was added dropwise. After addition, the reaction mixture was stirred at 0C for 10 minutes and then allowed to warm to room temperature. THE (150 mL) and Na2SO4 (40 g) were added, and the mixture was stirred for 18 h. The mixture was filtered overdicalite and washed with plenty of THE. The combined filtrates were evaporated under reduced pressure, and co-evaporated with toluene. The residue was crystallized from CH3CN (10 mL), filtered off, washed with CH3CN (2x), and dried under vacuum at 40C to provide a first fraction of 2-(2-(2-(benzyloxy)ethoxy)- 4-fluorophenyl)-1 -(6-fluoro-5-methyl-1 H-indol-3-yl)ethanone 7a (1 .86 g). Thefiltrate was evaporated under reduced pressure. The residue (7.7 g) was purified by flash chromatography (Stationary phase: Grace Reveleris silica 120 g, Mobile phase: heptane/EtOAc gradient 100/0 to 0/1 00). The fractions containing product were combined and left standing in an open recipient to allow evaporation of the solvent and crystallization of the product. The precipitate was isolated by filtration,washed 3x with heptane/EtOAc (1/1) and dried under vacuum at 40C to provide a second (1 .51 g) and third (0.75 g) fraction of intermediate 7a., 162100-95-0

162100-95-0 6-Fluoro-5-methyl-1H-indole 2774611, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; RABOISSON, Pierre Jean-Marie Bernard; BONFANTI, Jean-Francois; JONCKERS, Tim Hugo Maria; BARDIOT, Dorothee Alice Marie-Eve; MARCHAND, Arnaud Didier M; (70 pag.)WO2017/46258; (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.53924-05-3,7-Chloroindole,as a common compound, the synthetic route is as follows.,53924-05-3

General procedure: POCl3 (13.09 g, 85.36 mmol) was slowly added dropwise to DMF(10 mL) under ice bath. The mixture was stirred at ice bath for30 min. Then, DMF (6.24 g, 85.36 mmol) solution of indole (5 g,42.68 mmol) was added dropwise to the reaction system. Keepingthe reaction at room temperature for 3 h, ice water and 10% NaOHaq. were added into the reaction system to pH of 7-8 and continue to stir to a lot of white solid precipitation. The solid was recrystallizedfrom ethyl acetate and petroleum ether to obtain compound3 in yields of 97.6%.

53924-05-3 7-Chloroindole 104644, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Liu, Hong-Min; Suo, Feng-Zhi; Li, Xiao-Bo; You, Ying-Hua; Lv, Chun-Tao; Zheng, Chen-Xing; Zhang, Guo-Chen; Liu, Yue-Jiao; Kang, Wen-Ting; Zheng, Yi-Chao; Xu, Hai-Wei; European Journal of Medicinal Chemistry; vol. 175; (2019); p. 357 – 372;,
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

21296-93-5, 5-Chloro-2,3-dimethyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Organic urea catalyst (2S) -2-[[[[[3,5-bis (trifluoromethyl) phenyl] amino] oxomethyl] amino] -N- (diphenylmethyl) -N, 3,3-trimethylbutyramide (44.8 mg, 0.08 mmol), 2,3-dimethyl-5-chloroindole (71.8 mg, 0.4 mmol), diphenyl phosphate (9.8 mg, 0.04 mmol) and A molecular sieve (199.5 mg) was dissolved in n-hexane (16 mL), and then ethyl trifluoropyruvate (106 muL, 0.8 mmol) was added. The reaction was carried out at room temperature for 42.5 hours. The reaction equation is as follows:The reaction solution was filtered through silica gel, rinsed with ether, and concentrated. Silica gel column chromatography was used to obtain 112 mg of a solid product. The calculated yield was 80%. The measured er value was 93: 7, and n-hexane / dichloromethane (1: 1) was used. ) Recrystallization, mother liquor was concentrated to obtain 100 mg of liquid product, the calculated yield was 72%, and the er value was 96: 4., 21296-93-5

The synthetic route of 21296-93-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Hong Kong University Of Science And Technology Shenzhen Institute; Sun Jianwei; Ma Dengke; (35 pag.)CN110437126; (2019); 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

5192-03-0, 1H-Indol-5-amine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4,6-Dichloropyrimidine (5.89 g, 40 mmol), 5-aminoindole (6.27 g, 47 mmol) and N,N-diisopropylethylamine (20.6 ml, 0.12 mol) were dissolved in N-methylpyrrolidone (80 ml), and the reaction mixture was stirred at 50C for 2.5 hours. The reaction mixture was partitioned between ethyl acetate and water; the aqueous layer was subjected to re-extraction with ethyl acetate; and the combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure; a small amount of ethyl acetate was added to the residue to crystallize; and the crystals were filtered off, washed with diethyl ether, and dried under aeration to yield the title compound (3.70 g, 15 mmol, 38%) as white crystals. 1H-NMR Spectrum (DMSO-d6) delta (ppm): 6.42 (1H, m), 6.62 (1H, brs), 7.11 (1H, d, J=8.0 Hz), 7.35-7.40 (2H, m), 7.72 (1H, brs), 8.38 (1H, s), 9.68 (1H, s), 11.11 (1H, s)., 5192-03-0

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

Reference：
Patent; Eisai Co., Ltd.; EP1522540; (2005); 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