Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.117140-77-9,1H-Indole-2,5-dicarboxylic acid,as a common compound, the synthetic route is as follows.

117140-77-9, Example 34 1-Propyl-1H-indole-2,5-dicarboxylic acid 87 Sodium hydride (60% suspension, 125 mg, 5 mmol) was added to a stirred solution of 1H-indole-2,5-dicarboxylic acid (525 mg, 2 mmol) in dry DMF (10 mL) and maintained at ambient temperature for 1 hour. The reaction was cooled to 0 C. and then propyl bromide (0.275 mL, 3 mmol) was added. After 3 days the reaction was quenched by addition of 5% aqueous NH4Cl. The mixture was concentrated to dryness and then purified on a silica gel column using 5% EtOAc/toluene. The product was then dissolved in 30 mL ethanol and 10 mL of 2 M NaOH was added. The solution was heated at 55 C. for 2 days. The ethanol was removed in vacuo and the resulting aqueous solution was acidified with 0.01 M HCl to pH 3. The resulting precipitate was filtered and rinsed twice with water. The isolated product was dried by evaporation from absolute ethanol (3*) to give 340 mg (67%) of 87. 1H NMR (CDCl3): delta8.38 (s, 1H, H-4 indole), 7.87 (d, 1H, H-6 indole), 7.71 (d, 1 H, H-7 indole), 7.44 (d, 1 H, H-3 indole), 4.53 (m, 2H, Propyl), 1.7 (m, 2H, propyl), 0.81 (m, 3H, propyl) MS: 246 [M-H]

The synthetic route of 117140-77-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Dyatkina, Natalia B.; Shi, Dong-Fang; Roberts, Christopher Don; Velligan, Mark Douglas; Reinhard Liehr, Sebastian Johannes; Botyanszki, Janos; Zhang, Wentao; Khorlin, Alexander; Nelson, Peter Harold; Muchowski, Joseph Martin; US2003/212113; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.26807-73-8,1-Benzyl-1H-indol-5-amine,as a common compound, the synthetic route is as follows.

[Example 113] (1065) (1066) The mixture of 80 mg of 1-benzyl-1H-indol-5-amine, 100 mg of methyl 2-iodo-5-isopropylbenzoate, 15 mg of tris(dibenzylideneacetone)dipalladium(0), 19 mg of 4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene, 214 mg of cesium carbonate, and 2 mL of toluene, was heated at reflux for three hours and 10 minutes under a nitrogen atmosphere. The insoluble matter was filtered off and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate = 100:0-80:20) to give 122 mg of methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-isopropylbenzoate as a yellow oil. MS (ESI, m/z): 399 (N4+H)+., 26807-73-8

As the paragraph descriping shows that 26807-73-8 is playing an increasingly important role.

Reference£º
Patent; Toyama Chemical Co., Ltd.; FUJIFILM Corporation; TANAKA, Tadashi; KONISHI, Yoshitake; KUBO, Daisuke; FUJINO, Masataka; DOI, Issei; NAKAGAWA, Daisuke; MURAKAMI, Tatsuya; YAMAKAWA, Takayuki; EP2915804; (2015); 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.1000343-13-4,5-Bromo-6-methyl-1H-indole,as a common compound, the synthetic route is as follows.

5-Bromo-1,6-dimethyl-1H-indole (FJG. 2, compound 2) was synthesized as follows. A flame-dried round-bottom flask was charged with compound 14 (5.41 g, 25.8 mmol, 1.0 eq., FJG. 2) and anhydrous THF (50 mL). The solution was cooled in an ice-bath and treated with NaH as a 60%dispersion in mineral oil (1.24 g, 30.9 mmol, 1.2 eq.) and methyl iodide (3.2 mL, 51.5 mmol, 2.0 eq.). After stirring at 0 C for 2 hrs, the volatiles were removed under reduced pressure. The residue was dissolved with CH2C12 (100 mL) and washed with brine (50 mL). The organic fraction was (Na2SO4), filtered and concentrated to afford the crude product which was purified via flash chromatography on a silica column (7:193 v/v EtOAc:Hexanes) to afford the title compound as a yellow solid (4.56 g, 20.3 mmol, 79.1% yield). ?H NMR (500 MHz, Acetone-d6) 10.27 (bs, NH), 7.82 (s, 1H), 7.41 (s, 1H), 7.31 (dd, J= 3.2, 2.4 Hz, 1H), 6.45 (td, J= 2.1, 1.0 Hz, 1H), 2.48 (d, J= 0.8 Hz, 3H). ?3C NMR (125 MHz, Acetone-d6) 136.1, 129.7, 128.5, 126.0, 123.5, 115.6, 113.2, 101.1, 23.1. m.p. = 90-91 C. JR (neat):33143118, 3095, 1467, 1338 1753, 1705, 1614, 1507, 1468, 1270, 993, 881, 842, 730, 693, 606 cm?. HR-MS calculated for C,0H,0BrN [M+H] m/z 224.0075, found 224.0079., 1000343-13-4

The synthetic route of 1000343-13-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; CHANG, Christopher J.; BREWER, Thomas Francis; CHAN, Jefferson; (109 pag.)WO2017/34927; (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

344790-96-1, 5-Bromo-4-fluoro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-Bromo-4-fluoro-1H-indole obtained by the method described in Eur. J. Org. Chem. 2956-2969, 2006 (793 mg) was dissolved in N,N-dimethylformamide (30 ml), and bis(pinacolato)diboron (1.88 g), potassium acetate (1.82 g) and a [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride-dichloromethane complex (151 mg) were added. The mixture was stirred with heating under nitrogen atmosphere at 100 C. overnight. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane). The resulting colorless oil was slurry washed with hexane to give the title compound (481 mg) as a colorless solid.MS (EI) m/z: 261M+.1H-NMR (CDCl3) delta: 1.38 (12H, s), 6.65-6.68 (1H, m), 7.14-7.17 (1H, m), 7.18 (1H, s), 7.51 (1H, dd, J=8.3, 5.5 Hz), 8.27 (1H, brs).

344790-96-1, The synthetic route of 344790-96-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Daiichi Sankyo Company, Limited; US2011/82138; (2011); 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.58665-00-2,Methyl 2-(1-methyl-1H-indol-3-yl)acetate,as a common compound, the synthetic route is as follows.

58665-00-2, A solution of 2-(trifluoromethyl) aniline (161 mg, 1 mmol) in 5 ml of dry tetrahydrofuran was added via syringe to a vigorously stirred mixture of (L-METHYL-LH- indol-3-yl) -acetic acid methyl ester (4 mmol) and LDA (4 mmol, freshly prepared from DIISOPROPYLAMINE and n-BuLi) in 20 ml of dry THF AT-78 C under argon. The mixture was allowed to warm to room temperature and stirred for an additional 4 H. The resulting solution was concentrated in vacuo. The residue was partitioned between ETOAC, and concentrated aqueous NH4C1, and the aqueous layer was extracted with EtOAc. Combined organic extracts were dried over NA2S04, concentrated I71 vacuo, and purified by column chromatography (Silica gel, HEXANE/ETOAC = 1 : 3) to afford analytically pure 4-fluoro-3- (1-methyl-1H-indol-3-yl)-1H-quinolin-2-one.

The synthetic route of 58665-00-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; IMCLONE SYSTEMS INCORPORATED; WO2004/89930; (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

16732-70-0, Ethyl 5-bromo-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 5-bromoindole-2-carboxylic acid ethyl ester (3.48 g, 13 mmol), 4-terr-butylphenylboronic acid (4.63 g, 26 mmol), K3PO4 (9.93 g, 45 mmol), Pd(OAc)2 (146 mg, 0.65 mmol), tri-o-tolylphosphine (396 mg, 25 30 1.3 mmol), EtOH (20 ml) and toluene (10 mL) was stirred under argon for 20 min at rt foolowed by heating at 100 0C for 24 h. The mixture was allowed to cool to rt, poured into NaHCO3 (aq, sat) and extracted with EtOAc. The combined extracts were washed with water and brine, dried (Na2SO4), concentrated and purified by chromatography to give the sub-title compound (3.27 g, 78%)., 16732-70-0

The synthetic route of 16732-70-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOLIPOX AB; WO2006/77367; (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.1098340-27-2,Methyl 4-(trifluoromethyl)-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.,1098340-27-2

General procedure: Method B: to a solution of N-chlorosuccinimide (1.2 eq.) in DMF (0.3 M) was added sodium iodide (1.2 eq.) in small portion. The resulting brown solution was stirred at room temperature for 1 h before the slow addition at 0 C of the corresponding indole (1.0 eq.) in DMF (0.3 M). The reaction mixture was stirred at room temperature overnight. A saturated aqueous solution of sodium thiosulfate and water were added and the mixture was stirred for 1 h. After filtration, the crude material was washed with cold water and cold petroleum ether to afford after drying under high vacuum the attempted 3-iodoindole which was used in the next step without any further purification. Compounds 24 (method B), 22-35 (method A) were previously described [11], [18] and [19].

The synthetic route of 1098340-27-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Neagoie, Cleopatra; Vedrenne, Emeline; Buron, Frederic; Merour, Jean-Yves; Rosca, Sorin; Bourg, Stephane; Lozach, Olivier; Meijer, Laurent; Baldeyrou, Brigitte; Lansiaux, Amelie; Routier, Sylvain; European Journal of Medicinal Chemistry; vol. 49; (2012); p. 379 – 396;,
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.27018-76-4,1-Benzyl-1H-indole-3-carboxylic acid,as a common compound, the synthetic route is as follows.

1-benzyl-1 H-indole-3-carboxylic acid (1.4 g), tert-butyl piperazine- 1 -carboxylate (1.1 g)EDC (1.4 g), HOBt (1.0 g)And triethylamine (1.0 mL) were dissolved in dichloromethane (10 mL), And the mixture was stirred at room temperature for 19 hours.Water was added to the reaction solution, the mixture was extracted with dichloromethane and washed with saturated brine.The organic layer was dried over sodium sulfate,The solvent was evaporated under reduced pressure to obtain a residue,Purification by silica gel column chromatography (hexane-ethyl acetate), Tert-butyl 4- (1-benzyl-1 H-indole-3-carbonyl) piperazine- 1 – carboxylate1.5 g (yield 66%) was obtained., 27018-76-4

The synthetic route of 27018-76-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NATIONAL CENTER FOR GERIATRICS AND GERONTOLOGY; YANAGISAWA, KATSUHIKO; KAWAI, AKIYOSHI; (139 pag.)JP2017/171619; (2017); 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

165669-07-8, 7-Bromo-4-methyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(4-methyl-1 H-indol-7-yl)(phenyl)methanamine – To a solution of 1 -bromo-4-methyl-2-nitrobenzene (2.0 g, 9.26 mmol) in THF was added vinyl magnesium bromide 1 M in THF (27.8 ml_, 27.77 mmol) at – 50C. The reaction was finished after 1 h30. The reaction was quenched with sat. NH4CI. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated to dryness. The crude material was purified on silica gel column chromatography usinf hexanes/EtOAc (9:1 ) as eluent. A solution of the freshly synthesized 7-bromo-4-methyl-1 H-indole (1 .1 g, 5.24 mmol), zinc cyanide (860 mg, 7.32 mmol) and Pd(PPh3)4 (0.03 eq.) in DMF Ex.97 was heated under microwave irradiation at 170C for 1 h. After cooling, water was added to quench the reaction. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated under reduced pressure. The crude material was purified on silica gel column chromatography using hexanes/EtOAc (12:1 to 4:1 ) as eluent. The titled compound was then obtained following the modified procedure described in WO2006035157 (Protocol A) – Yield: 2% ; appearance: pale brown solid ; 1 H NMR, d (ppm) (Methanol d4) : 2.49 (s, 3H); 5.51 (s, 1 H); 6.47 (d, 1 H, J=3.2Hz); 6.81 (dd, 1 H, J=0.6Hz , J=7.3Hz); 7.01 (d, 1 H, J=7.3Hz); 7.17-7.22 (m, 2H); 7.25-7.31 (m, 2H); 7.39- 7.43 (m, 2H)

165669-07-8, As the paragraph descriping shows that 165669-07-8 is playing an increasingly important role.

Reference£º
Patent; GENFIT; DELHOMEL, Jean-Francois; WALCZAK, Robert; MAJD, Zouher; PIHAN, Emilie; BONNET, Pascal; PERSPICACE, Enrico; (198 pag.)WO2016/102633; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1224724-39-3,Methyl 4-bromo-1H-indole-7-carboxylate,as a common compound, the synthetic route is as follows.

To a solution of methyl 4-bromo-1H-indole-7-carboxylate (6 g, 23 mmol, Preparation 1 step B) in THF (300 mL), water (60 mL) and MeOH (60 mL) was added lithium hydroxide (2.83 g, 118 mmol). Then the mixture was heated to reflux overnight. After cooling to rt, the solvent was removed under reduced pressure, the aqueous layer was acidified by addition of 4 N HC1 to about pH 6. The precipitate was filtered, and the solid was dried to provide 4-bromo-]H-indole-7-carboxylic acid (5.5g, 97%): ?H NMR (DMSO-d6) 3 11.39 (br, 1H), 7.65-7.63 (d, J= 8.0 Hz, 1H), 7.46-7.44 (m, 1H), 7.33-7.31 (d, J= 8.0 Hz, 1H), 6.49-6.48 (m, 1H)., 1224724-39-3

The synthetic route of 1224724-39-3 has been constantly updated, and we look forward to future research findings.

Reference£º
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