Day: March 22, 2022

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

923197-75-5, (6-Bromo-1H-indol-2-yl)methanol is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

923197-75-5, General procedure: To a stirred solution of the crude (1H-indol-2-yl)methanol (1.07 g, 7.3 mmol) in anhydrous CH2Cl2(10 mL) at coldbath temperature (~10 .) was added portionwise pyridinium chlorochromate (PCC) (1.89 g, 8.1mmol). Reaction was stirred at ambient temperature for 2 hours. Reaction was diluted with CH2Cl2 and filteredthrough a pad of celite and washed with CH2Cl2. After evaporation of solvent, crude product was silica-columnchromatographed (Biotage) using Acetone: Hexane as an eluent to yield 1H-indole-2-carbaldehyde (2d) (0.43 g,41% yield).

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：
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
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

1059630-08-8, (4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 : To a degassed mixture of (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro- lH-pyrido[4,3-b]indole-2(9bH)-carboxylate (1.60 g, 8.0 mmol), 2-chloro-2,2-di- deuteri oacetam i de (2.5 g, 26 mmol), and KI (2.68 g, l6mmol) in dioxane (30 mL), diisopropylethylamine (3.0 mL, 16 mmol) is added at room temperature. The reaction mixture is then heated to 104 C under vigorous stirring for 5 days. Solvents are removed under vacuum and the residue is suspended in dichloromethane (50 mL) and extracted with water (20 mL). The organic phase is separated, dried over anhydrous K2CO3 and (0280) concentrated to a residue. The product is purified by silica gel column chromatography using a gradient of 0 – 100% ethyl acetate in hexanes to obtain (4aS,9bR)-ethyl 5-(2-amino- 1 , 1 -di- 2-oxoethyl)-6-bromo-3,4,4a,5-tetrahydro-lH-pyrido[4,3-b]indole-2(9bH)-carboxylate as a brown oil (1.26 g, yield 41%). MS (ESI) m/z 384.1 [M+l]. The synthesis of the starting material is disclosed in US 2010/113781. The reaction scheme is shown below:

1059630-08-8, The synthetic route of 1059630-08-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; INTRA-CELLULAR THERAPIES, INC.; LI, Peng; ZHANG, Qiang; DAVIS, Robert; (63 pag.)WO2019/183341; (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

289483-82-5, 4-Methyl-7-nitro-1H-indole-3-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

PRODUCTION EXAMPLE 12 7-Amino-3-cyano-4-methyl-1H-indole 12.6 g (62.6 mmol) of the compound of Production Example 6 was dissolved in a mixed solution of 100 ml of tetrahydrofuran and 100 ml of methanol, and the mixture was hydrogenated at an ordinary temperature under 3 atoms in the presence of 430 mg (1.87 mmol) of platinum oxide. The catalyst was filtered off and the filtrate was concentrated to dryness. Then, a mixed solution of tert-butyl methyl ether and hexane was added to the residue and the crystals were collected by filtration, to give 10.7 g of the title compound. 50.5 g (186 mmol) of the compound of Production Example 11 was dissolved in 400 ml of dichloromethane. In nitrogen atmosphere, 210 ml (2.76 mol) of trifluoroacetic acid was added thereto at 0 C., followed by stirring at room temperature for 40 minutes. The reaction mixture was adjusted to pH 7 by adding a 5N aqueous sodium hydroxide thereto. The solvent was removed, and then the residue was extracted with ethyl acetate. The organic layer was successively washed with water and brine, dried over magnesium sulfate and concentrated to dryness. A mixed solution of diethyl ether and hexane was added to the residue and the crystals were collected by filtration, to give 24.5 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.47(3H, s), 5.07(2H, s), 6.34(1H, d, J=7.6 Hz), 6.64(1H, d, J=7.6 Hz), 8.10(1H, s), 11.70(1H, br s)

289483-82-5, As the paragraph descriping shows that 289483-82-5 is playing an increasingly important role.

Reference：
Patent; Wakabayashi, Toshiaki; Funahashi, Yasuhiro; Hata, Naoko; Semba, Taro; Yamamoto, Yuji; Haneda, Toru; Owa, Takashi; Tsuruoka, Akihiko; Kamata, Junichi; Okabe, Tadashi; Takahashi, Keiko; Nara, Kazumasa; Hamaoka, Shinichi; Ueda, Norihiro; US2004/18192; (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

676273-39-5, 3-Iodo-1-tosyl-1H-indole-5-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

676273-39-5, Compound 15 (10 g), Thiophene boronic acid and K2CO3 were taken in Dioxane (120 ml): Wa- ter(15ml) mixture in a two neck RB flask equipped with Nitrogen balloon and reflux condenser. Reaction mass was degassed for 20 min. Palladium catalyst was added and reaction mass was again degassed for 3 min. Reaction mixture was refluxed at 110C for 2 hrs under Nitrogen. Re- action progress was monitor by TLC. After completion of the reaction, the mixture was filtered through a bed of celite. Filtrate was diluted with ethyl acetate. Ethyl acetate layer was washed with water and brine and concentrated. Crude material was taken in 80 ml methanol and stirred for 45 min at RT. Solid obtained is filtered and wash with cold methanol to get 8.4 g white solid product. (0863) 1H NMR (300 MHz, DMSO-d6) delta 8.50 (s, 1H), 8.40 (s, 1H), 8.22- 8.08 (m, 2H), 7.98 (d, J = 8.3 Hz, 2H), 7.82 (d, J = 8.7 Hz, 1H), 7.70 (d, J = 1.8 Hz, 2H), 7.41 (d, J = 8.2 Hz, 2H), 2.31 (s, 3H).

The synthetic route of 676273-39-5 has been constantly updated, and we look forward to future research findings.

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