Electric Literature of 951625-93-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.951625-93-7, name is Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, molecular formula is C9H7ClN2O2, molecular weight is 210.62, as common compound, the synthetic route is as follows.
[0168] To a solution of methyl 4-chloro-lH-pyrrolo[2,3-b]pyridine-5-carboxylate (2.3 g, 11 mmol) in dimethylformamide (DMF; 20 mL) was added NaH (0.67 g, 17 mmol, 60% purity) under nitrogen. The mixture was stirred at 0 C for 0.5 hours. To this was added chloromethyl methyl ether (1.1 g, 13 mmol, 1 mL) and the reaction was stirred at 25 C for 2 hours. Upon completion, the reaction mixture was quenched by addition aqueous saturated NH4C1 solution (20 mL) and diluted with water (10 mL). The mixture was extracted with ethyl acetate (3x 40 mL). Organic layers were combined, washed with brine (2x 25 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give methyl 4-chloro-l-(methoxymethyl)-lH-pyrrolo[2,3-b]pyridine-5- carboxylate (2.3 g, 8.6 mmol, 78% yield) as a yellow solid.
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Reference:
Patent; SYROS PHARMACEUTICALS, INC.; ZHANG, Yi; AUSTGEN, Kathryn; CHUAQUI, Claudio Edmundo; MALOJCIC, Goran; SINKO, William; GUAN, Huiping Amy; SAVOIE, Tracey Lodie; (92 pag.)WO2018/191587; (2018); A1;,
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