Day: March 25, 2022

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.32588-36-6,Indole-2-acetic acid,as a common compound, the synthetic route is as follows.

General procedure: For compounds of group C, 0.5 mmol 2-propynylaminewas usedto form amides with corresponding carboxylic acid derivativesmediated by N,N0-dicyclohexylcarbodiimide (DCC, 1.0 eq.) in dryacetonitrile (MeCN). Conditions and procedures used here weresame as these in group A. Afterwards, different amides were mixedwith 4-azidophenol (1.0 eq), fresh prepared solutions of CuSO4 (0.1eq) in demi-water (0.20 mL), sodium ascorbate (0.20 eq) in demiwater(0.20 mL) in MeOH (4 mL). The reaction mixture was leftstirring overnight for at 60 C. The CuAAC reaction and purificationwere also done in the same way as for group A described above., 32588-36-6

32588-36-6 Indole-2-acetic acid 4371752, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Chen, Deng; Dekker, Frank J.; Fokkens, Marieke; Kok, Tjie; Poelarends, Gerrit J.; Proietti, Giordano; Xiao, Zhangping; van Merkerk, Ronald; European Journal of Medicinal Chemistry; vol. 186; (2020);,
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

2795-41-7, 6-Fluoroindole-3-carboxaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of glyoxalylhydrazide 18 (1.47mmol) and aldehyde 20 or 22 (1.47mmol) in ethanol (5mL) was refluxed for 6h. After completion of the reaction, ethanol was distilled off and the residue was taken into water (10mL) and allowed to stir at room temperature for 30min. The obtained suspension was filtered, washed with water and dried to obtain yellow solid ketohydrazide-hydrazones 21a-o and 23a-e in 88-96% yields., 2795-41-7

The synthetic route of 2795-41-7 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Tantak, Mukund P.; Klingler, Linus; Arun; Kumar, Anil; Sadana, Rachna; Kumar, Dalip; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 184 – 194;,
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

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

343-90-8, 1-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 46: Intermediate 47–Diethyl [ (5-fluoro-lH-indol-3-yl) methyl] (methyl) malonate [0431] A solution of 5-fluorogramine (15. 5g, 80. 6MMOL) in acetonitrile (450mL) was treated with diethyl methylmalonate (20. 8mL, 121MMOL) and tributylphosphine at reflux for 17 hours. The cooled reaction is concentrated under reduced pressure and dissolved in ethyl acetate (1. 5L), washed with 1N aqueous HC1 (500ML), saturated aqueous NaCl (500ML), dried over MgS04 and concentrated under reduced pressure to an orange oil. Chromatography ( (3 : 1) hexane-EtOAc) afforded 16. 5g (64%) of desired product as an oil which solidifies on standing to a white solid: mp 76-77 C., 343-90-8

As the paragraph descriping shows that 343-90-8 is playing an increasingly important role.

Reference：
Patent; WYETH; WO2005/12291; (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

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

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

21296-93-5, 5-Chloro-2,3-dimethyl-1H-indole is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,21296-93-5

General procedure: In a flame dried flask the imidate (1.0 equiv) was dissolved in anhydrous 1,2-dichloroethane(0.15 M) followed by the addition of the indole (1.5 equiv). To this solution freshly distilledTMSOTf (0.2 equiv) was added and the resulting mixture was stirred at rt for 3 h. The reactionmixture was then quenched with the addition of 1M NaOH. The organic layer was separated andthe aqueous layer was extracted with DCM (2x). The combined organic extracts were dried oversodium sulfate, filtered and concentrated. The residue was then purified by silica gelchromatography using the solvent systems listed for each compound.

21296-93-5 5-Chloro-2,3-dimethyl-1H-indole 2772413, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Article; Adhikari, Arijit A.; Radal, Lea; Chisholm, John D.; Synlett; vol. 28; 17; (2017); p. 2335 – 2339;,
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