Sodium hydride → N-Methoxy-N-methyl-1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

Participants

Reaction Steps

A solution of N-Methoxy-N-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide (300 mg, 1.46 mmol) in DMF (5 mL) was cooled to in an ice bath and sodium hydride (73 mg of 60% dispersion, 1.83 mmol) added in one portion. The mixture was stirred for 5 minutes then triisopropylsilyl chloride (353 mg, 1.83 mmol) added dropwise. The reaction was then stirred for 14 hrs during which time the temperature reached rt. The reaction was then quenched by pouring into a mixture of ice and 25% ammonium chloride solution (50 mL). The resulting mixture was then extracted with EtOAc (2×20 mL) and the combined extracts washed with water (10 mL) and brine (10 mL) then dried over magnesium sulfate. Subsequent filtration and concentration afforded a yellow oil. This crude oil was considered sufficiently pure to carry forward directly. Yield=92%

Provenance & Evidence