Indole Building Blocks

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.115666-47-2,6-Iodo-1H-indole,as a common compound, the synthetic route is as follows.

6-Iodo-1H-indole (2, 1.513 g,6.30 mmol, 1.00 equiv, [S2]) was dissolved in CH2Cl2 (90 mL). Boc2O (2.063 g, 9.45 mmol,1.50 equiv) and DMAP (154 mg, 1.26 mmol, 20 mol %) were added and the mixture wasstirred at room temperature overnight. The solvent was evaporated and the crude productwas subjected to column chromatography using petroleum ether/EtOAc (15:1) as the eluentto yield N-Boc-6-iodoindole (3, 2.117 g, 6.17 mmol, 98%) as colorless solid.

115666-47-2, The synthetic route of 115666-47-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Marsch, Nils; Kock, Mario; Lindel, Thomas; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 334 – 342;,
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

91348-45-7, Ethyl 3-bromo-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,91348-45-7

Production Example 9-1 ethyl 3-(3-furyl)-1H-indole-2-carboxylate A toluene-ethanol mixed solvent (1:1, 60 mL) containing commercially available ethyl 3-bromo-1H-indole-2-carboxylate (1.5 g), 3-furylboronic acid (939 mg), tetrakis(triphenylphosphine)palladium(0) (1.29 g) and a 1 M aqueous sodium carbonate solution (11.2 mL) was heated under reflux overnight at 100 C. under a nitrogen atmosphere. The reaction solution was concentrated under reduced pressure, and to the residue, water was added and the solution was extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1), whereby the title compound (340 mg) was obtained as a pale yellow solid.

91348-45-7 Ethyl 3-bromo-1H-indole-2-carboxylate 4715017, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; MSD K.K; US2012/28990; (2012); 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.348640-06-2,4-Bromo-7-azaindole,as a common compound, the synthetic route is as follows.

j0695j To a solution of 4-bromo-1H-pyrrolo[2,3-bjpyridine (XCI) (5 g, 25.4 mmol, 1 eq.), DMAP (311 mg, 2.55 mmol, 0.1 eq.) and TEA (5.3 mL, 38 mmol, 3 eq.) in DCM (100 mL) was added Boc2O (7.2 mL, 31 mmol, 1.2 eq.) at 0C. The reaction was warmed to room temperature and stirred for 2 h. Water (100 mL) was added and extracted with DCM (x 2). Removal solvents gave tert-butyl 4-bromo-1H-pyrrolo[2,3-bjpyridine-1-carboxylate (XCII) as a colorless oil (6.95 g, 23.4 mmol, 92.1% yield). ?H NMR (CDC13, 400 MHz) ppm 1.60 (s, 9H), 6.50 (d, J=4Hz, 1H), 7.31 (d,J=5.2Hz, 1H), 7.63 (d,J=4Hz, 1H), 8.23 (d,J=5.2Hz, 1H); ESIMS found for C,2H,3BrN2O2 mlz 297.1 (M+H).

348640-06-2, The synthetic route of 348640-06-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (274 pag.)WO2017/24021; (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

126811-29-8, 7-Bromo-4-chloro-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7-Amino-3,4-dichloro-1H-indole 7-Bromo-4-chloro-1H-indole obtained from 2-bromo-5-chloronitrobenzene in the same manner as in Production Example 1a was first chlorinated in the same manner as in Production Example 3a, and then the bromo group was converted into an amino group, to give the title compound. 1H-NMR(DMSO-d6) delta (ppm): 5.26(2H, s), 6.29(1H, d, J=8.1 Hz), 6.74(1H, d, J=8.1 Hz), 7.45-7.51(1H, m), 11.08-11.27(1H, m), 126811-29-8

As the paragraph descriping shows that 126811-29-8 is playing an increasingly important role.

Reference£º
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.877-03-2,5-Bromo-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.

877-03-2, 5-bromoindole-3-carbaldehyde 2 (10 mmol) was dissolved in acetonitrile and to this powdered NaOH (5 mmol) was added and stirred for 10 min. Methyl iodide (10 mmol) was added dropwise to the reaction mixture. After 3h of stirring at room temperature, the solvent was completely evaporated. It was extracted with ethyl acetate (3×20 ml) and dried over Na2SO4. The combined organic layer was concentrated in vacuo to give a light yellow color solid purified by recrystallization with diethyl ether. Pale yellow solid; Yield: 96%; mp 122-124 C; IR (KBr) numax 3103, 2923, 2813, 1700, 1654. 1533, 1467, 1369, 1083, 799, 726; 1H NMR (DMSO-d6, 300 MHz) delta 9.88 (s, 1H), 8.33 (s, 1H), 8.23 (d, J = 1.70 Hz, 1H), 7.60 (d, J = 8.68 Hz, 1H), 7.48 (dd, J = 2.08, 8.87 Hz, 1H), 3.89 (s, 3H); TOF-HRMS (m/z) for C10H8BrNO, calculated 237.9862, observed 237.9855 [M+1] +

The synthetic route of 877-03-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Prajapti, Santosh Kumar; Nagarsenkar, Atulya; Guggilapu, Sravanthi Devi; Gupta, Keshav Kumar; Allakonda, Lingesh; Jeengar, Manish Kumar; Naidu; Babu, Bathini Nagendra; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 3024 – 3028;,
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.14805-29-9,exo-Hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione,as a common compound, the synthetic route is as follows.

Example 2To the reaction mixture containing Compound (C) which was obtained in the above Example 1 were added tetra-n-butyl ammonium hydrogen sulfate (0.62 g, 1.83 mmol), (3aR,4S,7R,7aS)-hexahydro-4,7-methano-2H-isoindole-1,3-dione [Compound (D)] (11.3 g, 68.4 mmol), potassium carbonate (7.6 g, 55.0 mmol) and water (0.4 g), and the resulting mixture was reacted under reflux for 3 hours. Then, the reaction mixture was cooled to room temperature, and water (200 g) was added to the mixture. The mixture was separated with a separating funnel, and the toluene layer was washed with 2.3percent (W/W) brine (175 g). Further, active carbon (0.9 g) was added to the toluene solution, and the mixture was stirred for 1 hour. The active carbon was removed by filtration to give a toluene solution containing (3aR,4S,7R,7aS)-2-{(1R,2R)-2-[4-(1,2-benzisothiazol-3-yl)-piperazin-1-ylmethyl]cyclohexylmethyl}-hexahydro-4,7-methano-2H-isoindole-1,3-dione (2-[[(1R,2R)-2-[[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]methyl]-cyclohexyl]methyl]hexahydro-(3aS,4R,7S,7aR)-4,7-methano-1H-isoindole-1,3(2H)-dione) [Compound (E)] (266.5 g). The yield of Compound E was 94.3percent. The yield of Compound (E) was calculated based on the analytical result that the content of the compound in the toluene solution was 7.9percent (w/w) (which was calculated by LC absolute calibration curve method). And, the production rate of by-product (R) was 0.12percent (which was calculated with the above formula (a))., 14805-29-9

As the paragraph descriping shows that 14805-29-9 is playing an increasingly important role.

Reference£º
Patent; Dainippon Sumitomo Pharma Co, Ltd.; US2011/263847; (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.1092114-59-4,3-Iodo-1H-indole-5-carbonitrile,as a common compound, the synthetic route is as follows.

5-cyanoindole (4.0 g, 28.1 mMol) was dissolved in DMF (20 mL) and potassium hydroxide (4.74 g, 84.4 mMol) was added. The reaction was cooled in a water bath at 10 C. and iodine (7.12 g, 28.1 mMol) was added. After stirring for 30 min the reaction was poured into water (100 mL) with sodium thiosulfate (2 g). The resulting solid 5-cyano-3-iodo-lindole was collected by filtration and recrystallized from ethyl acetate and hexanes.The crystals were dissolved in acetonitrile (60 mL) and N,N-diisopropylethylamine (5.64 mL, 32.3 mMol) and solid p-toluenesulfonyl chloride (6.17 g, 32.3 mMol) was added. After stirring for 1 h, the reaction was poured into water (100 mL) and the resulting solids were collected. The material was recrystallized from hot ethyl acetate/hexanes to provide the product as white needles (7.92 g, 67%): 1H NMR (400 MHz, CDCl3) delta 8.06 (1H, d, J=9.2 Hz), 7.79 (3H, m), 7.73 (1H, d, J=1.5 Hz), 7.61 (1H, dd, J=8.6, 1.5 Hz), 7.29 (2H, d, J=8.5 Hz), 2.38 (3H, s); MS m/e 454.9 (M+Na)., 1092114-59-4

As the paragraph descriping shows that 1092114-59-4 is playing an increasingly important role.

Reference£º
Patent; Denhart, Derek John; Ditta, Jonathan L.; King, Dalton; Macor, John E.; Marcin, Lawrence R.; Mattson, Ronald J.; Meng, Zhaoxing; US2004/63768; (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.348640-06-2,4-Bromo-7-azaindole,as a common compound, the synthetic route is as follows.

D23,4-dibromo-lH-pyrrolo[2,3-b]pyridineA mixture of 4-bromo- lH-pyrrolo[2,3-b]pyridine (1.00 g, 5.08 mmol) and NBS (0.918 g, 5.16 mmol) in DCM (20.0 mL) was stirred at 0 C for 1.5 hour. The resulting suspension was filtered, washed with DCM, residue collected, dried in a 50 C oven overnight to afford the title compound (1.014 g). LCMS (A): m/z (M+H)+ 277, C7H4Br2N2 requires 276 (basic)., 348640-06-2

As the paragraph descriping shows that 348640-06-2 is playing an increasingly important role.

Reference£º
Patent; GLAXO WELLCOME MANUFACTURING PTE LTD; CHEN, Deborah, W.; DUNCAN, Sarah; KING, Nigel, Paul; LEE, Kiew, Ching; MAK, Sing, Yeung; RIVERS, Dean, Andrews; WO2012/170752; (2012); 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

39974-94-2, 5-Methoxy-1-methyl-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-Methoxy-1-methyl-1H-indole-3-carbaldehyde [76 g, Reference Example 2(a)] and hydroxylamine hydrochloride (55.9 g) were stirred together in dimethylformamide (900 mL) under reflux for 1 hour. The mixture was allowed to cool, then poured into water and then extracted with ethyl acetate. The combined extracts were washed with water then evaporated to give the title compound (53 g) as a pale brown solid, m.p. 100-104 C. 1H NMR [(CD3)2SO]: delta 8.17 (1H, s); 7.54 (1H, d, J=9.0 Hz); 7.09 (1H, d, J=2.4 Hz); 6.97 (1H, dd, J=9.0 and 2.4 Hz); 3.82 and 3.84 (6H, s)., 39974-94-2

39974-94-2 5-Methoxy-1-methyl-1H-indole-3-carbaldehyde 925973, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Cox, Paul J.; Majid, Tahir N.; Lai, Justine Y.Q.; Morley, Andrew D.; Amendola, Shelley; Deprets, Stephanie D.; Edlin, Christopher; US2004/9983; (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.33588-64-6,Ethyl 2-(1H-indol-2-yl)acetate,as a common compound, the synthetic route is as follows.

Separately, hydroxylamine solution (hydroxylamine hydrochloride(541.3 mg, 7.80 mmol, 7.80 eq.) And methanol (2.7 mL)),And sodium hydroxide solution (sodium hydroxide(475 mg, 11.5 mmol, 11.5 eq) and methanol (1.6 mL)).Sodium hydroxide solution was added to the hydroxylamine solution,And the mixture was stirred at 0 C. for 45 minutes.After filtering the obtained solution,The filtrate was added to ethyl 2- (1H-indol-2-yl) acetate(199.5 mg, 1.00 mmol, 1.00 eq.), And the mixture was stirred at room temperature for 15 minutes.After addition of acetic acid, the product was extracted with ethyl acetate.The organic layer was washed with water and brine, dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure.The obtained solution was purified by silica gel column chromatography (chloroform / methanol (10/1, Rf = 0.20)),A light brown solid target substance (Y-011) was obtained (yield 66%)., 33588-64-6

As the paragraph descriping shows that 33588-64-6 is playing an increasingly important role.

Reference£º
Patent; NAGOYA UNIVERSITY; ITAMI, KENICHIRO; KINOSHITA, TOSHINORI; HAGIHARA, SHINNYA; TAKAHASHI, KOJI; YOSHIMURA, MASAHIKO; (27 pag.)JP2015/89885; (2015); 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