With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.165669-07-8,7-Bromo-4-methyl-1H-indole,as a common compound, the synthetic route is as follows.
To a mixture of potassium hydride (4.47 g, 34.27 mmol, 30 wt %) suspended in anhydrous tetrahydrofuran (80 mL) was added 7-bromo-4-methyl-1H-indole (6.00 g, 28.56 mmol) dissolved in tetrahydrofuran (30 mL) at 0 C. After 15 minutes, the mixture was cooled to -70 C. and t-BuLi (1.3 M, 54.9 mL) was added dropwise, keeping the temperature below -65 C. After further 15 minutes, carbon dioxide gas (15 psi pressure) was bubbled into the reaction and the reaction was slowly warmed to rt over 30 minutes. On completion, the reaction mixture was quenched with ice water (120 mL), and washed with ethyl acetate (3¡Á60 mL). The aqueous phase was collected and acidified with 1 N hydrochloride acid solution until the pH<7. Then, the mixture was extracted with ethyl acetate (3¡Á60 mL). The organic phase was collected, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude product as a brown solid. The crude product was triturated with petroleum ether:dichloromethane (10:1, 100 mL) to give the product (3.50 g, 69% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 12.82 (br s, 1H), 11.02 (br s, 1H), 7.67 (d, J=7.6 Hz, 1H), 7.35 (t, J=2.8 Hz, 1H), 6.92 (d, J=7.6 Hz, 1H), 6.56 (dd, J=2.0, 3.2 Hz, 1H), 2.54 (s, 3H)., 165669-07-8
The synthetic route of 165669-07-8 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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