Tag: M.W:200-300

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.289483-82-5,4-Methyl-7-nitro-1H-indole-3-carbonitrile,as a common compound, the synthetic route is as follows.

289483-82-5, Example 2A; Synthesis of 7-amino-3-cyano-4-methyl-1H-indole; After suspending 400 g (1.99 mol) of the 3-cyano-4-methyl-7-nitro-1H-indole obtained in Example 1A in a mixture of 6 L of ethyl acetate and 6 L of methanol, the suspension was subjected to hydrogenation in the presence of 40 g of 10% palladium-carbon at ordinary temperature, 4 atmospheres. After removing the catalyst by filtration, the filtrate was treated with activated carbon and concentrated to give crude crystals. The crude crystals were dissolved in 6 L of 1,2-dimethoxyethane at an external temperature of 60 C., and then 12 L of water was added dropwise. Upon confirming precipitation of crystals, the mixture was stirred for 1.5 hours while cooling in an ice bath and filtered, and the crystals were washed twice with water (1 L). The crystals were air-dried at 50 C. for 16 hours to give 289 g of the title compound (yield: 84.8%). HPLC analysis confirmed that the obtained compound was identical to the 7-amino-3-cyano-4-methyl-1H-indole described in WO00/50395. (HPLC conditions) Mobile phase: CH3CN/H2O/70% HClO4=400/600/1 (v/v/v) Flow rate: 1.0 mL/min Detection: UV (282 nm) Column: YMC-Pack Pro C18 250×4.6 mm

The synthetic route of 289483-82-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Hayashi, Kenji; Abe, Taichi; Ozeki, Naoki; Akamatsu, Hiroshi; US2007/37854; (2007); 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

6855-64-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6855-64-7,2-Phenyl-1H-indol-5-amine,as a common compound, the synthetic route is as follows.

Example 5 Compound 5 N-(2-phenyl-1H-indol-5-yl)acetamidine Prepared in a manner similar to that of Example 1. Yield: (63percent); Elem. anal. C16H15N3 M.W.: 249.31; theory C, 77.08; H, 6.06; N, 16.85. found C, 76.97; H, 6.29; N, 16.85. IR (KBr): 3434, 3024, 1634, 1597 cm-1; 1H-NMR (d6-DMSO) 7.8-6.3 (m, 9H); 1.8 (s, 3H).; Example 7 Compound 5 As an alternative to the method described in Example 5, this product may be prepared as reported below: N-(2-phenyl-1H-indol-5-yl)acetamidine Prepared in a manner similar to that of Example 5. Yield: 60percent; Elem. anal. C16H15N3; theory C, 77.08; H, 6.06; N, 16.85. found C, 77.17; H, 5.89; N, 16.68. IR (KBr): 3434, 3024, 1634, 1597 cm-1; 1H-NMR (d6-DMSO) 7.8-6.3 (m, 9H); 1.8 (s, 3H).

The synthetic route of 6855-64-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; ROTTAPHARM SPA; US2005/197331; (2005); 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

923197-75-5,923197-75-5, (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

Compound TDI01155-2 (600 mg, 2.65 mmol) was dissolved in acetonitrile (20 mL), MnO2 (692 mg, 7.96 mmol)was added, and the reaction was stirred at room temperature overnight. Thin layer chromatography (petroleum ether :ethyl acetate=5:1) and LC-MS assay indicated the reaction was complete. The reaction solution was concentrated underreduced pressure, and the residue was purified by column chromatography (petroleum ether : ethyl acetate= 10:1 to1:1) to afford compound TDI01155-3 (520 mg, yellow solid, yield: 87.6%).1HNMR (400 MHz, CDCl3) delta 9.86 (s, 1H), 9.22 (s, 1H), 7.65 (s, 1H), 7.61 (d, J = 8.4 Hz, 1H), 7.30-7.28 (m, 1H), 7.25(br, 1H). MS m/z (ESI): 224.0/226.0 [M+H].

As the paragraph descriping shows that 923197-75-5 is playing an increasingly important role.

Reference：
Patent; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (235 pag.)EP3421465; (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.393553-57-6,6-Bromo-4-methoxy-1H-indole,as a common compound, the synthetic route is as follows.

393553-57-6, To a stirred solution of 6-bromo-4-methoxy-lH-indole A.85(1.80 g, 7.98 mmol) in acetic acid (21 mL) at room temperature was added NaBH3CN (1.5037 g, 23.93 mmol) and the mixture was stirred at room temperature for 1 hour. To the mixture was added water (100 mL) and the mixture was cooled to 0 0C. The mixture was made basic with 10 N aqueous NaOH (35 mL) to pH 14. The mixture was extracted with ether (50 mL x 3). The combined organic layers were washed with water (50 mL x 2) and brine (50 mL x 2), dried over K2CO3, filtered, and concentrated under reduced pressure to give 6-bromo- 4-methoxyindoline A.86 (1.56 g, 85.7% yield) as a brown oil: 1H NMR (500 MHz, DMSO-d6) delta ppm 6.34 (1 H, d, J=I.4 Hz), 6.29 (1 H, d, J=I.4 Hz), 5.71 (1 H, s), 3.72 (3 H, s), 3.39 – 3.46 (2 H, m), 2.76 (2 H, t, J=8.7 Hz); Mass Spectrum (ESI) m/e = 228.1 [M+l (79Br)] and 230.1 [M+l (81Br)].

The synthetic route of 393553-57-6 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; AMGEN INC.; WO2009/158011; (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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14618-45-2,3-(Trifluoroacetyl)indole,as a common compound, the synthetic route is as follows.

Reference Production Example 32-1 3-(trifluoroacetyl)-1H-indole-1-ylmethanol The mixture of 4.80 g of 3-(trifluoroacetyl)-1H-indole, 1.35 g of paraformaldehyde and 0.10 g of triethylamine was stirred at 130 C for 2 hours. After the reaction mixture was cooled to room temperature, acetone was added to the reaction mixture. The mixture was filterd, and then the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and hexane was added to the residue, as a result, a crystal was formed. The crystal was collected to obtain 5.36 g of 3-(trifluoroacetyl)-1H-indole-1-ylmethanol. 1H-NMR(DMSO-d6,TMS,delta(ppm)):5.71(2H, d),6.92(1H,t),7.36-7.43(2 H,m),7.76(1H,d),8.19(1H,d),8.31(1H,s), 14618-45-2

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

Reference：
Patent; Sumitomo Chemical Company, Limited; EP1710234; (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

101861-63-6, 4,6-Dichloroindole-2-carboxylic acid is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1. 4,6-Dichloro-2-(N-methoxy-N-methylamino)carbonyl]indole The title compound was prepared according to the procedure described in step 1 of Example 7 from 4,6-dichloroindole-2-carboxylic acid (Salituro, Francesco G. et al., J. Med. Chem., 1990, 33, 2944). 1H-NMR (DMSO-d6) delta: 12.09 (1H, br s), 7.48 (1H, dd, J=1.0, 1.6 Hz), 7.25 (1H, d, J=1.6 Hz), 7.11 (1H, s), 3.82 (3H, s), 3.63 (3H, s)., 101861-63-6

101861-63-6 4,6-Dichloroindole-2-carboxylic acid 127988, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Nakao, Kazunari; Stevens, Rodney William; Kawamura, Kiyoshi; Uchida, Chikara; Koike, Hiroki; Caron, Stephane; US6608070; (2003); B1;,
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

40899-71-6, 1-(Phenylsulfonyl)-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of i-Pr2NH (3.5 mL, 25 mmol) in THF was added 1.64 M solution of n-BuLi inn-hexane (14.4 mL, 24 mmol) at -78 C, and the mixture was stirred at 0 C for 30 min. After thereaction mixture was cooled to -78 C, a solution of S6 (3.0 g, 12 mmol) in THF (20 mL) wasadded. The mixture was stirred at -78 C for 1.5 h, and then at 0 C for 1 h. To this reactionmixture was added I2 (3.0 g, 12 mmol) at -78 C, and the mixture was stirred at ambienttemperature for 20 h. The reaction was quenched with 3% aqueous solution of Na2CO3 and themixture was extracted with EtOAc. The combined organic layers were washed with water andbrine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified bycolumn chromatography on silica gel (n-hexane-EtOAc 20:1) to give a 2:1 mixture of 2-iodinatedS6 and unreacted S6 (3.66 g). To a solution of the obtained mixture (3.66 g) in dioxane (37 mL)was added NaOt-Bu (1.0 g, 11 mmol) at ambient temperature, and the mixture was stirred at 80 Cfor 3 h. The reaction was quenched with water, and the mixture was extracted with EtOAc. Thecombined organic layers were dried over MgSO4 and concentrated under reduced pressure. Theresidue was purified by column chromatography on silica gel (n-hexane-EtOAc 100:1) to give2-iodo-1H-indole (S7, 1.6 g, 6.6 mmol, 55%) as a colorless solid., 40899-71-6

The synthetic route of 40899-71-6 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Kudoh, Takayuki; Fujisawa, Syo; Kitamura, Megumi; Sakakura, Akira; Synlett; vol. 28; 16; (2017); p. 2189 – 2193;,
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

900514-08-1, 5-Chloro-3-iodo-7-azaindole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,900514-08-1

Step 2; -Preparation of 5-chloro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (4)To 5-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (2, 16.50 g, 59.25 mmol) in 250.0 mL of N,N-dimethylformamide, sodium hydride (3.10 g, 77.5 mmol) is added. The reaction is stirred at room temperature for 90 minutes, then triisopropylsilyl chloride (3, 13.00 mL, 61.36 mmol) is added slowly. The reaction is stirred at room temperature overnight, then poured into water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (4, 10.0 g).

As the paragraph descriping shows that 900514-08-1 is playing an increasingly important role.

Reference：
Patent; Zhang, Jiazhong; Ibrahim, Prabha N.; Spevak, Wayne; Tsai, James; Ewing, Todd; Zhang, Ying; Zhang, Chao; US2011/263595; (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.434958-85-7,N-Boc-5-Hydroxyindole,as a common compound, the synthetic route is as follows.,434958-85-7

General procedure: A suspension of bismacycle tosylate 1-OTs (1.0 equiv.; initial concentration = 0.05 M),K2CO3 (1.2 equiv.) and arylboronic acid (1.1 equiv.) in toluene/water (99:1,v/v) was stirred at 60 C for 2 h. After cooling to room temperature, substrates(naphthols, 0.90 equiv.; phenols, 3.0 equiv.) and mCPBA (titrated; 1.5 equiv.) were added. The reaction was stirred for 10 min at room temperature and then methanol (2 ml) was added. The mixture was diluted with diethyl ether and washed witha saturated aqueous solution of KHCO3. The organic phase was separated, dried (MgSO4), filtered and concentrated in vacuo before purification by flash column chromatography on silica gel. Following isolation of the desired arylation product, bismacycle acetate 1-OAc can be recovered by flushing the column with diethyl ether to remove organic impurities before elution with 2% acetic acid in methanol.

434958-85-7 N-Boc-5-Hydroxyindole 22596220, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Ball, Liam T.; Jurrat, Mark; Lewis, William; Maggi, Lorenzo; Nature Chemistry; vol. 12; 3; (2020); p. 260 – 269;,
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.16732-69-7,Ethyl 7-bromo-1H-indole-2-carboxylate,as a common compound, the synthetic route is as follows.

General procedure: A mixture of lactam(1.0 eq),bromide(2.0 eq),Cul(0.5 eq),(trans)-1,2-N,Ndimethylaminocyclohexane(1.0 eq),and K2C03(2.5 eq) in toluene(1 mL) was sparged withArgas for 5 min. The reaction mixture was sealed and heated to 110 C for 18 h. Same workup and purification protocols described in general coupling procedure A were followed toobtaine a desire product., 16732-69-7

16732-69-7 Ethyl 7-bromo-1H-indole-2-carboxylate 7017885, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; VANDERBILT UNIVERSITY; LEE, Taekyu; TARR, James, C.; JEON, Kyuok; SALOVICH, James, M.; SHAW, Subrata; VEERASAMY, Nagarathanam; KIM, Kwangho; CHRISTOV, Plamen, P.; OLEJNICZAK, Edward, T.; ZHAO, Bin; FESIK, Stephen, W.; BIAN, Zhiguo; (526 pag.)WO2017/152076; (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