Carbon Dioxide → HCID 68109550, compound

Participants

Reaction Steps

To a solution of the product of step C (300 mg, 0.62 mmol) in tetrahydrofuran (1.5 mL) was added isopropylmagnesium chloride (1 M in tetrahydrofuran) (0.75 mL, 0.75 mmol) dropwise under an argon atmosphere at −20° C. over 5 min. The reaction mixture was stirred at −15° C. to −10° C. for 1 h before dry CO2 gas was bubbled through the reaction mixture over 15 min. The reaction mixture was slowly allowed to reach to ambient temperature and stirred overnight. The mixture was quenched with aqueous saturated ammonium chloride solution (10 mL) and extracted with dichloromethane. The organic extract was dried over sodium sulfate, filtered and concentrated in vacuo to give 8-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine-6-carboxylic acid (125 mg, 50%) as a white solid. The crude product was directly used for the next step.

Provenance & Evidence