Month: March 2022

288385-93-3, 4-Fluoro-5-methoxy-2-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-fluoro-5-methoxy-2-methylindole (709 mg, 3.95 mmol) in methylene chloride (9 ml) cooled at -30 C. was added a solution of boron tribromide (2.18 g, 8.7 mmol) in methylene chloride (1 ml). After stirring for 1 hour at ambient temperature, the mixture was poured onto water and was diluted with methylene chloride. The pH of the aqueous layer was adjusted to 6. The organic layer was separated, washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography, eluding with ethyl acetate/petroleum ether (3/7) to give 4-fluoro-5-hydroxy-2-methylindole (461 mg, 70%). MS-ESI: 166 [MH]+ 1H NMR Spectrum: (DMSOd6) 2.35 (s, 3H); 6.05 (s, 1H); 6.65 (dd, 1H); 6.9 (d, 1H); 8.75 (s, 1H); 10.9 (s, 1H) 13C NMR Spectrum: (DMSOd6) 13.5; 94,0; 106,0; 112; 118.5 (d); 132 (d); 136 (d); 136.5; 142.5 (d), 288385-93-3

288385-93-3 4-Fluoro-5-methoxy-2-methyl-1H-indole 22030728, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Hennequin, Laurent Francois Andre; US2003/212055; (2003); 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

676273-39-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.676273-39-5,3-Iodo-1-tosyl-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

Compound 15 (0.682 g), [2-(trifluoromethyl)-3-thienyl] boronic acid (0.38 g) and 2N solution of Na2CO3 (0.514 g, 2.4ml) were taken in n-Butanol (5ml) in a RB flask. Resulting mixture was de- gassed for 10 min. To this, was added PdCl2(PPh3)2 (0.057 g) and again degassed for 5 min. Resulting reaction mixture was stirred and heated at 110C for 2 hrs under nitrogen atmos- phere. Reaction completion was monitored by TLC. After completion of reaction it was cooled to RT. Filtered the reaction through celite bed and washed with ethyl acetate. Filtrate was washed with water and brine. Organic layer was dried over Na2SO4 and evaporated completely. Crude compound was purified by flash column chromatography. Pure compound was eluted with 10- 25% ethyl acetate in heptane. Evaporated solvent under vacuum. It was concentrated under vacuum to afford 0.25 g (34.70%) of the desired product 18. 1H NMR (300 MHz, DMSO-d6) delta 8.20 (d, J = 8.7 Hz, 1H), 8.11 (d, J = 4.9 Hz, 2H), 8.05- 7.95 (m, 3H), 7.84 (dd, J = 8.7, 1.4 Hz, 1H), 7.51 (dd, J = 5.1, 1.4 Hz, 1H), 7.44 (d, J = 8.2 Hz, 2H), 2.34 (s, 3H).

As the paragraph descriping shows that 676273-39-5 is playing an increasingly important role.

Reference：
Patent; BASF SE; POONOTH, Manojkumar; RHEINHEIMER, Joachim; RATH, Rakesh; ROSENBAUM, Claudia; WIEBE, Christine; BRAHM, Lutz; RUDOLF, Georg Christoph; KHANNA, Smriti; HADEN, Egon; ROEHL, Franz; SIEPE, Isabella; KREMZOW-GRAW, Doris; SCHIFFER, Helmut; (199 pag.)WO2018/210659; (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.879-37-8,Indole-3-acetamide,as a common compound, the synthetic route is as follows.,879-37-8

To a solution of 5, 6-dihydro-4H-pyrrolo [3,2,1-//] 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 O0C was added a solution of potassium t-butoxide (IM 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-?)’] quinolin-l-yl)-4(lH-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, IH), 7.78(s, IH), 7.63(d, IH, J=2.8 Hz), 7.44(s, IH), 7.35(d, IH, J=8 Hz), 7.16(d, IH, J=8.4 Hz), 7.1 l(t, IH, J=7.6 Hz), 6.86 (t, IH, J=7.6 Hz), 6.80(d, IH, J=7.2 Hz),6.64(t, IH, J=8 Hz), 6.57(d, IH, J=8 Hz), 4.2(t, 2H, J=6 Hz), 2.96(t, 2H, J=6 Hz), 2.24(m, 2H).

As the paragraph descriping shows that 879-37-8 is playing an increasingly important role.

Reference：
Patent; ARQULE, INC.; WO2006/86484; (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.14618-45-2,3-(Trifluoroacetyl)indole,as a common compound, the synthetic route is as follows.

14618-45-2, General procedure: One of compounds 3a-3f (20 mmol) was dissolved in DMF (10 mL). Trifluoroacetic anhydride (4.2 mL, 30 mmol) was added dropwise at 0C. After stirring for 3.5 h, water was added, the solid filtered off and treated with 20% NaOH (40 mL, 0.2 mol) at 55C overnight. Upon cooling down, the solution was extracted with Et2O. The aqueous phase was acidified with concentrated HCl and the residue was filtered off to give one of compounds 4a-4f. 1H-Indole-3-carboxylic acid (4a). White solid, yield 81%, mp 216-218C (214C [20]). 1H NMR spectrum, delta, ppm: 7.15 t (J = 8.0 Hz, 2H, ArH), 7.45 d (J = 8.0 Hz, 2H, ArH), 8.00 s (1H, CH-N), 11.81 s (1H, COOH), 11.93 s (1H, NH).

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

Reference：
Letter; Zhang; Xu; Wang; Kang; Russian Journal of General Chemistry; vol. 87; 12; (2017); p. 3006 – 3016;,
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

20289-27-4, 7-(Benzyloxy)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 7-benzyloxy-1H-indole (1.0 g, 4.5 mmol) in DMF (30 mL) stirred at 0 C. under N2 was treated with NaH (215 mg, 5.4 mmol). After 30 min, CH3I (1.3 g, 9.0 mmol) was added. The reaction was warmed up to RT and stirred for 1 hour. The reaction mixture was quenched with water and extracted with DCM (25 mL*2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting with PE) to give the title compound as a colorless oil in 94% yield. 1H NMR (300 MHz, CDCl3): delta 7.42-7.40 (m, 2H), 7.36-7.29 (m, 3H), 7.09 (d, J=8.1 Hz, 1H), 6.90 (d, J=2.7 Hz, 1H), 6.86 (t, J=7.8 Hz, 1H), 6.62 (d, J=7.5 Hz, 1H), 6.32 (d, J=3.0 Hz, 1H), 5.06 (s, 2H), 3.92 (s, 3H). LCMS (M+H)+238.

20289-27-4, The synthetic route of 20289-27-4 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; CELGENE QUANTICEL RESEARCH, INC.; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kanouni, Toufike; Stafford, Jeffrey Alan; Veal, James Marvin; Wallace, Michael Brennan; (250 pag.)US2017/298040; (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

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

399-51-9, General procedure: A round-bottomed flask containing (28mL, 370mmol) freshly distilled dimethylformamide (DMF) was cooled to 0C for about 30min and freshly distilled phosphorus oxychloride (8.41mL, 90mmol) was subsequently added with stirring to the DMF over a period of 30min. A solution of indole 19 (85.47mmol) in DMF (10mL, 130mmol) was added to the yellow solution over a period of 1h. The solution was stirred at room temperature till it become a yellow paste. At the end of the reaction, 30g of crushed ice was added to the paste with stirring to make a clear cherry-red aqueous solution. Sodium hydroxide solution (1N, 100mL) was added dropwise with stirring to this cherry-red solution. The resulting suspension was heated rapidly to 90C and allowed to cool at room temperature, after which it was refrigerated for overnight. The product was filtered, washed with water (2×100mL) and air-dried to afford pure indole-3-carboxaldehydes 20 in 80-90% yields. Indole-3-carboxaldehyde, pale yellow solid; mp 194-196C (Lit. [37]196-197C).

399-51-9 6-Fluoro-1H-indole 351278, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Tantak, Mukund P.; Klingler, Linus; Arun; Kumar, Anil; Sadana, Rachna; Kumar, Dalip; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 184 – 194;,
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

1167055-46-0, 4-Bromo-1H-indole-7-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-bromo-1H-indole-7-carbonitrile (3 g, 13.57 mmol, Sinova) in EtOH (36.2 mL)/DMSO (9.05 mL) was slowly added added hydrogen peroxide (28.0 mL, 274 mmol) and NaOH (28.0 mL, 28.0 mmol). The reaction mixture was stirred at rt for about 1 h. Water was added and the precipitate was collected by filtration, washed with water, and dried under vacuum to provide 4- bromo-]H-indole-7-carboxamide (2.85 g, 88%). LC/MS (Table 1, Method R = 1.42 mm; MS m/z:280 (M+MeCN)., 1167055-46-0

As the paragraph descriping shows that 1167055-46-0 is playing an increasingly important role.

Reference：
Patent; ABBVIE INC.; BONAFOUX, Dominique; DAVIS, Heather, M.; FRANK, Kristine, E.; FRIEDMAN, Michael, M.; HEROLD, J., Martin; HOEMANN, Michael, Z.; HUNTLEY, Raymond; OSUMA, Augustine; SHEPPARD, George; SOMAL, Gagandeep, K.; VAN CAMP, Jennifer; VAN EPPS, Stacy, A.; VASUDEVAN, Anil; WALLACE, Grier, A.; WANG, Lu; WANG, Zhi; WILSON, Noel, S.; XU, Xiangdong; WO2014/210255; (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

7506-66-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7506-66-3,cis-Hexahydro-1H-isoindole-1,3(2H)-dione,as a common compound, the synthetic route is as follows.

Cis-8-azabicyclo[4,3,0]nonane To a slurry of lithium aluminium hydride (17.1 g) in dry diethyl ether (375 ml) under a nitrogen atmosphere, cis-hexahydrophthalimide (23.0 g) in dry tetrahydrofuran (300 ml) was added over a two-hour period. The mixture was refluxed for 2.5 hours, cooled and treated very slowly with excess of water. The precipitate was filtered off and the filtrate was evaporated to yield the title compound as a viscous oil, which was used in the next step without purification.

7506-66-3 cis-Hexahydro-1H-isoindole-1,3(2H)-dione 6992236, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Leo Pharmaceutical Products Ltd. A/S; US4181659; (1980); 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.6127-17-9,6-Chloro-2-methyl-1H-indole,as a common compound, the synthetic route is as follows.,6127-17-9

D. 6-Chloro-2-methyl-1H-indole-3-acetic acid methyl ester. As in Example 1, Part E, 2.2 g (0.0133 mole) of 6-chloro-2-methyl-1H-indole was treated with 8.3 mL (0.0133 mol) of a 1.6M solution of n-butyl lithum in hexane, 14 ml (0.014 mol) of a 1M solution of ZnCl2 in ether, and 1.26 mL (0.0133 mol) of methyl 2-bromoacetate to give after chromatography on silica (gradient, toluene?10% EtOAc/toluene) 2.1 g (66%) of 6-chloro-2-methyl-1H-indole-3-acetic acid methyl ester as an oil. Analyses: Calc’d for C12 H12 ClNO2: C, 60.64; H, 5.09; N, 5.89. Found: C, 60.78; H, 5.10; N, 5.84.

As the paragraph descriping shows that 6127-17-9 is playing an increasingly important role.

Reference：
Patent; Eli Lilly and Company; US5578634; (1996); 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.170147-29-2,tert-Butyl 5-(benzyloxy)-1H-indole-1-carboxylate,as a common compound, the synthetic route is as follows.

Example 93B; 5 -Hydroxy-indole- 1-carboxylic acid tert-butyl ester; [0464] A solution of the product of Example 93 A (680 mg, 2.103 mmol) in ethanol (20 mL) was treated with 10% palladium-on-carbon (68 mg) and ammonium formate (265 mg, 4.205 mmol), and stirred at room temperature under a nitrogen atmosphere for 1 hour. The reaction was filtered through a 0.45 mu PTFE membrane and the catalyst washed with methanol. The filtrate was concentrated by rotary evaporation under vacuum and the residue taken up in ethyl acetate (50 mL), washed with water (2 x 25 mL) and brine (25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title compound as a white solid (475 mg, 96%).

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

Reference：
Patent; ABBOTT LABORATORIES; WO2007/76034; (2007); 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