Water → methyl 2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

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Reaction Conditions

Reaction Steps

Lithium hexamethyldisilazide (3.6 mL, 3.6 mmol, 1M in THF) was added to a solution of 2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (0.57 g, 3.04 mmol; see WO 2008/034860) in THF (20 mL) at −78° C. The reaction mixture was stirred at −78° C. for 5 minutes, then warmed up to 0° C. for 30 minutes, and finally warmed to room temperature for another 30 minutes. The mixture was cooled back to −78° C. where methyl chloroformate (0.35 mL, 4.55 mmol) was added dropwise. The mixture was slowly warmed up to room temperature and stirred for 16 hours. Water was then added, followed by dichloromethane. The layers were separated. The aqueous layer was extracted twice with dichloromethane. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude was purified by flash chromatography to afford methyl 2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (0.45 g, 61%).

Provenance & Evidence