Indole Building Blocks

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4769-97-5,4-Nitroindole,as a common compound, the synthetic route is as follows.,4769-97-5

General procedure: Sodium hydride (1.2 g, 50 mmol) was added portionwise to a solution of 4-nitroindole 1 (8.2 g, 50 mmol) in abs. DMF (50 mL) cooled in an ice bath. Methyl iodide (3.27 mL, 55 mmol) or corresponding alkyl bromide (55 mmol) was added dropwise and the reaction stirred for 4 h at room temperature with TLC analysis monitoring for the completion of the reaction. The solvent was removed under vacuum and the residue partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate and the solvent evaporated to give residue. 1-Methyl-4-nitro-1H-indole (2). Yellow solid, mp 112-113, yield 95%. 1H NMR (300 MHz, DMSO-d6) delta 8.09 (d, 1H, J = 8.7 Hz, H-5), 7.99 (d, 1H, J = 8.7 Hz, H-7), 7.76 (d, 1H, J = 3.0 Hz, H-2), 7.36 (t, 1H, J = 8.1 Hz, H-6), 7.03 (d, 1H, J = 3.0 Hz, H-3), 3.93 (s, 3H, CH3-1). Calcd. for C9H8N2O2: C, 61.36; H, 4.58; N, 15.90; Found: C, 61.50; H, 4.30; N, 15.70%.

The synthetic route of 4769-97-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Halaiev, Olexandr; Garazd, Myroslav; Gzella, Andrzej; Lesyk, Roman; Tetrahedron Letters; vol. 58; 13; (2017); p. 1324 – 1325;,
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

5457-28-3, 1H-Indole-3-carbonitrile is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5457-28-3, General procedure: Enone 1a (62.5 mg, 0.3 mmol), 3-cyanoindole (51.2 mg, 0.36mmol, 1.2 equiv), KOH (0.8 mg, 0.015 mmol, 5.0 mol%), and CH2Cl2 (3.0 mL) were sequentially charged into a dry round-bottomedflask (25 mL). The reaction mixture was stirred at 25 Cuntil the reaction complete (monitored by TLC). The reactionmixture was diluted with CH2Cl2 (3.0 mL), and washed withbrine (3 ¡Á 4.0 mL). The aqueous phase was extracted withCH2Cl2 (4.0 mL). The organic phase was combined, dried withanhydrous Na2SO4, and concentrated under reduced pressure.The residue was purified by flash column chromatography onsilica gel (PE-EtOAc, 6:1) to afford the pure product 2a.

The synthetic route of 5457-28-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Yang, Jingya; Li, Tianyuan; Zhou, Hongyan; Li, Nana; Xie, Dongtai; Li, Zheng; Synlett; vol. 28; 10; (2017); p. 1227 – 1231;,
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

166104-19-4, tert-Butyl 5-nitro-1H-indole-1-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tert-butyl 5-nitro-1H-indole-1-carboxylate (525 mg, 2.0 mmol) in ethyl acetate (8 ml) was added 10percent palladium on carbon (50 mg). Stir overnight at room temperature in a hydrogen atmosphere. Suction filteration, The filtrate was evaporated under reduced pressure to give a white solid (469 mg, 100percent), 166104-19-4

As the paragraph descriping shows that 166104-19-4 is playing an increasingly important role.

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wen Liang; Zheng Jinfu; Zhang Jin; Wu Shoutao; Yuan Xiaofeng; Lin Runfeng; Wang Xiaojun; Zuo Yinglin; Zhang Yingjun; (21 pag.)CN104311541; (2017); B;,
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

3189-22-8, 7-Methoxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 7-methoxyindole (1 eq) in DMF cooled in an ice bath was added NaH (60% dispersion in oil, 1.2 eq). The reaction was stirred for 1 hr at room temperature then recooled in an ice bath. Benzenesulfonyl chloride (1.1 eq) was added then the reaction was stirred for 2 hrs at room temperature. Water/ethyl acetate were added and the ethyl acetate layer was washed repeatedly (3x) with water. The ethyl acetate layer was concentrated and evaporated to dryness., 3189-22-8

The synthetic route of 3189-22-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SYNTA PHARAMACEUTICALS CORP.; WO2008/112199; (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

1953-54-4, 5-Hydroxyindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Benzylbromide (2.0 mL, 16.8 mmol) and K2CO3 (3.1 g, 22.5 mmol) were added to a solution of 5-hydroxyindole 1 (2.0 g, 15.0 mmol) in DMF (10 mL) and the mixture was stirred and heated at reflux. After 24 h, the mixture was cooled to r.t. and the reaction was quenched with 10% aq HCl. The mixture was extracted with EtOAc (3 50 mL), MgSO4. The solvent was removed and the residue was purified by silica gel column chromatography (EtOAc/hexane, 1:6) to give 2. Yield: 3 g (91%); colorless solid; mp 97-100 C (CHCl3). IR (CHCl3): 3483, 1626, 1581, 1477, 1452, 1281, 1153 cm-1. 1H NMR (500 MHz, CDCl3): delta = 8.03 (br. s, 1H), 7.52 (d, J = 7.5 Hz, 2 H), 7.43 (t, J = 7.5 Hz, 2 H), 7.36 (t, J = 7.5 Hz, 1H), 7.27 (d, J = 8.6 Hz, 1H), 7.24 (d, J = 2.3 Hz, 1H), 7.15 (t, J = 2.8 Hz, 1H), 6.99 (dd, J = 8.6, 2.3 Hz, 1H), 6.51 (t, J = 2.3 Hz, 1H), 5.15 (s, 2 H). 13C NMR (125 MHz, CDCl3): delta = 153.5, 137.8, 131.3, 128.7, 128.4, 127.9, 127.7, 125.1, 113.2, 111.9, 104.1, 102.5, 71.1. HRMS (EI): m/z [M+] calcd for C15H13NO: 223.0997; found: 223.1028., 1953-54-4

1953-54-4 5-Hydroxyindole 16054, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Article; Abe, Takumi; Haruyama, Tomohiro; Yamada, Koji; Synthesis; vol. 49; 18; (2017); p. 4141 – 4150;,
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.618910-07-9,8-Methoxy-5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole,as a common compound, the synthetic route is as follows.

General procedure: To degassed tetrahydrofuran (5 mL) was added chloro-(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1 ,1 ‘-biphenyl)[2-(2-aminoethyl)phenyl]palladium(ll)-methyl-f-butyl ether adduct (PdRuPhos G1 ) (0.017 g, 0.024 mmol), 2-dicyclohexylphosphino-2?,6’-diisopropoxybiphenyl (RuPho) (0.011 g, 0.024 mmol), the title compound from Preparative Example 2 (0.05 g, 0.024 mmol), and the commercially available 4-(6-bromobenzo[d]thiazol-2-yl)morpholine (0.073 g, 0.029 mmol). Then, a 1 M solution of lithium bis(trimethylsilyl)amide (LiHMDS) in tetrahydrofuran (1 mL, 1 mmol) was added. The resulting reaction mixture was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature, dissolved in dichloromethane (100 mL). The organic phase was washed with water and brine and dried over Na2S04. The solvent was removed under reduced pressure. The crude product was purified on a silica gel column using a Biotage Isolera One purification system employing an ethyl acetate/n-heptane gradient (80/20 => 100/0) to afford the title compound (0.070 g, 69 %)., 618910-07-9

618910-07-9 8-Methoxy-5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 24206808, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; AC IMMUNE SA; NAMPALLY, Sreenivasachary; GABELLIERI, Emanuele; MOLETTE, Jerome; (220 pag.)WO2019/134978; (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.169674-01-5,5,6-Difluoroindole,as a common compound, the synthetic route is as follows.

23a) 5,6-Difluoro-1H-indole-3-carbaldehyde Phosphoryl cloride (22.03 g, 143.67 mmol) was added drop wise to an ice-cold N,N-dimethylformamide (DMF) (19.10 g, 261.22 mmol) and the mixture was stirred for 0.5 h at 0-5 C and for 1 h at room temperature. Then the mixture was cooled to 0-5 C and a solution of 5,6-difluoro-1H-indole (20.00 g, 130.61 mmol) in DMF (20 g) was added drop wise. The resulting mixture was stirred for 0.5 h at 0-5 C and for 15 h at room temperature. The mixture was poured onto chopped ice (200 g) and alkalinized with NaOH to pH=10. The crystalline product was filtered off, washed with water and dried to provide the title comound (22.72 g, 96.01 %).

169674-01-5, The synthetic route of 169674-01-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1932831; (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

244-76-8, 9H-Pyrido[2,3-b]indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A round bottom flask was charged with 9H-pyrido [2,3-b] indole (3.5 g, 21 mmol)1-bromo-4-iodobenzene (8.83 g, 31 mmol), copper (I) iodide (0.8 g, 4.2 mmol),(¡À) -trans-1,2-diaminocyclohexane (0.48 g, 4.2 mmol),Potassium phosphate tribasic (8.9 g, 42 mmol) was added and dissolved in 160 ml of toluene.Was refluxed and stirred for 24 hours. Thin layer chromatography (TLC) andAfter confirming by HPLC, the reaction was terminated. After filtration, the column (MC: Hex = 1: 4)To obtain a solid compound (5.19 g, yield = 75%)., 244-76-8

The synthetic route of 244-76-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LG Display Co., Ltd.; Choi Hye-ok; Lee Seung-jae; Pin Jong-gwan; Seo Bo-min; (39 pag.)KR2018/44695; (2018); 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.15317-58-5,1H-Indole-3-carbohydrazide,as a common compound, the synthetic route is as follows.

General procedure: 1H-Indole-3-carboxylate methylester 2 (1.0 mmol-equiv.) was refluxed with hydrazine hydrate(12.5 g, 0.25 M) in appropriate ethanol (30 mL) for 2 h. The progressof the reaction was monitored by TLC. After cooling the reactionmixture to room temperature, the mixtures were filtered to givewhite solid crude products without purification. Next, indolehydrazide(3, 1.0 mmol) in ethanol (30 mL) was added dropwiseinto the appropriate aldehyde (1.5 mmol-equiv.) and a few drops ofpropionic acid; the mixture was stirred and refluxed for 2.5 h. Aftercooling, the precipitates were filtered and washed several times bymethanol to yield the crystal substances 4aeu.

15317-58-5, As the paragraph descriping shows that 15317-58-5 is playing an increasingly important role.

Reference£º
Article; Ju, Zhiran; Su, Mingzhi; Hong, Jongki; La Kim, Eun; Moon, Hyung Ryong; Chung, Hae Young; Kim, Suhkmann; Jung, Jee H.; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 86 – 98;,
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

348-36-7, Ethyl 5-fluoro-1H-indole-2-carboxylate is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6.1. Ethyl 2-(ethoxycarbonyl)-5-fluoro-alpha-methylene-1H-indole-3-acetate. A solution of 37.2 g (180 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 25.8 g (222 mmol) of ethyl pyruvate and 31 ml of concentrated sulphuric acid in 400 ml of acetic acid is stirred for 20 h. The solvent is evaporated under reduced pressure, the residue is taken up in water and ethyl acetate, the organic phase is separated, washed with a dilute aqueous ammonia solution and then with a saturated aqueous sodium chloride solution and dried over sodium sulphate, and the solvent is evaporated under reduced pressure. 37.1 g (122 mmol) of solid product are obtained, which product is used as is in the following stage.

348-36-7, 348-36-7 Ethyl 5-fluoro-1H-indole-2-carboxylate 2727899, aindole-building-block compound, is more and more widely used in various fields.

Reference£º
Patent; Synthelabo; US6075021; (2000); 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