Tag: M.W:200-300

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

General procedure for preparation of XY; A solution of XInt01 (1 eq), K2CO3 (5 eq) and alkyl halides Y such as methyl iodide, ethyl iodide, n-propyl bromide, iso-propyl bromide, n-butyl bromide, isobutyl bromide (1.5 eq, 1 h) or O-t-butyldimethylsilyl-2-chloroethanol (10 eq, 24 h) or O-t-butyldimethylsilyl-2-chloropropanol in acetone was stirred and heated to reflux. After completion of the reaction (monitored by thin layer chromatography (TLC)), the mixture was concentrated in vacuo and the residue treated with dichloromethane. The insoluble impurities were removed by filtration and the filtrate was concentrated to afford compound XY (60-95% yield).; Example 6; N-(cyclopentylmethyl)-1-methyl-1H-indole-3-carboxamide; Synthesised according to the procedure disclosed in Example 1 where X is indole, Y is methyl iodide and Z is cyclopentylmethyl amine. Formula: C16H20N2O; Molecular Weight: 256.3; Mass/charge ratio: 256.2 (100.0%), 257.2 (18.3%), 258.2 (1.8%); Elemental analysis: C, 74.97; H, 7.86; N, 10.93; O, 6.24., 14618-45-2

The synthetic route of 14618-45-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; AFFECTIS PHARMACEUTICALS AG; US2009/312366; (2009); 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

1186663-64-8, 3-Bromo-1H-indole-4-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1186663-64-8, Step 2: Preparation of Intermediate 3-Bromo-1-methyl-1H-indole-4-carbonitrile (I-146b)3-Bromo-1H-indole-4-carbonitrile (I-146a: 500 mg, 2.272 mmol) was added dropwise to a stirred mixture of NaH (0.218 g, 9.0833 mmol) in dry DMF (15 mL) at 0 C. over a period of 10 minutes. This was followed by the addition of methyl iodide and the resulting mixture was stirred at 0 C. for 2 hours. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mixture was quenched with ice water; the precipitate formed was collected and dried to afford 0.400 g of the crude product.1H NMR (CDCl3, 300 MHz): delta 7.8-7.0 (m, 4H), 3.82 (s, 3H)

As the paragraph descriping shows that 1186663-64-8 is playing an increasingly important role.

Reference：
Patent; Novartis AG; US2010/331326; (2010); 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.101861-63-6,4,6-Dichloroindole-2-carboxylic acid,as a common compound, the synthetic route is as follows.

4,6-Dichloro-1H-indole-2-carboxylic acid (500 mg, 2.17 mmol), N,0- dimethylhydroxylamine hydrochloride (423 mg, 4.34 mmol), HOBt (332 mg, 2.17 mmol), EDC hydrochloride (874 mg, 4.56 mmol) and triethylamine (1.32 mL, 8.68 mmol) were dissolved in anhydrous dimethylformamide (40 mL). The mixture was stirred for overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water, saturated NLLCl, 10% NaOH and brine. The organic layer was dried over Na2S04, and it was concentrated under reduced pressure. The residue was purified on an ISCO chromatograph (0-50% ethyl acetate/hexane) to give product as a white solid (505 mg, 85%); ‘H NMR (300 MHz) (DMSO-de) d 12.10 (bs, 1H), 7.45 (d, J= 1 Hz, 1H), 7.24 (d, J= 1 Hz, 1H), 7.09 (s, 1H), 3.80 (s, 3H), 3.33 (s, 3H).

101861-63-6, The synthetic route of 101861-63-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; TAXIS PHARMACEUTICALS, INC.; LAVOIE, Edmond, J.; SAGONG, Hye Yeon; PARHI, Ajit, K.; (144 pag.)WO2019/99402; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.885519-01-7,6-Bromo-4-chloro-1H-indole,as a common compound, the synthetic route is as follows.

885519-01-7, To a solution of 6-bromo-4-chloro-lH-indole (1 g, 4.34 mmol) in N,N-dimethylformamide (10 ml) and cooled to 0C was added sodium hydride (0.208 g, 5.21 mmol) and the reaction mixture was stirred at 0C during 1 hour. Benzenesulfonyl chloride (0.668 ml, 5.21 mmol) was added and rhe reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with a saturated NH4CI solution and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 5-40% ethyl acetate in cyclohexane) to give 6- bromo-4-chloro-l-(phenylsulfonyl)-lH-indole (1.57 g, 98%) as a beige solid. LC/MS (Method i) Rt = 2.71 min.; no ionisation NMR (DMSO-d6, 300MHz): delta 8.05 (m, 4H), 7.75 (m, 1H), 7.65 (m, 3H), 6.90 (dd, J=3.8, 0.8 Hz, 1H)

The synthetic route of 885519-01-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ABBVIE INC.; ARGIRIADI, Maria A.; BREINLINGER, Eric; CUSACK, Kevin P.; HOBSON, Adrian, D.; POTIN, Dominique; BARTH, Martine; AMAUDRUT, Jerome; POUPARDIN, Olivia; MOUNIER, Laurent; KORT, Michael, E.; (392 pag.)WO2016/198908; (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

1065181-58-9, Ethyl 5-bromo-1H-indole-7-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 59:Ethyl S-bromo-S^jtheta-dimethyltetrahydro^H-thiopyran^-ylJ-IH-indole-y-carboxylate.2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293g, 2.03mmol) was dissolved in dichloromethane (35ml_) in an oven dried flask containing 3 A molecular sieves and stirred under argon at 0 0C. TMS-OTf (0.451 g, 2.03mmol, 0.36 ml.) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1 /-/-indole-7-carboxylate (0.293g, 2.031 mmol) was dissolved in DCM (1OmL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10 0C. The reaction was cooled to 0 0C and triethylsilane (0.353 g, 0.485 ml_, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212g (26%) of the the title compound. LC/MS: m/z 397 (M+H), Rt 1.51 min.

1065181-58-9, 1065181-58-9 Ethyl 5-bromo-1H-indole-7-carboxylate 59332585, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/118724; (2008); 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

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

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

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

6127-19-1, 6-Bromo-2-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6127-19-1, 6-bromo-2-methyl-1H-indole (250 mg, 1.19 mmol), KOAc (410 mg, 4.2 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (520 mg, 2.0 mmol) and PdCl2(dppf)CH2Cl2 (50 mg, 0.061 mmol) were taken up in 1,4-dioxane (7 mL) under Ar. The stirred reaction mixture was heated to 105 C. and stirred for 14 h. The reaction mixture was diluted with water, EtOAc and brine and the phases were separated. The organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (10-60% EtOAc in hexanes) to afford 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (7.50).

The synthetic route of 6127-19-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); 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