Isobutyronitrile → 2-(5-Bromopyridin-2-yl)-2-methylpropanenitrile

Participants

Reaction Conditions

Reaction Steps

2,5-Dibromopyridine (2 g, 8.44 mmol) was placed in a vial that was evacuated and backfilled with argon three times. Anhydrous dioxane (8.4 ml) was then added and the suspension was stirred. In a separate vial, 2-methylpropanenitrile (0.76 ml, 8.44 mmol) was added to a solution of sodium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (28.1 ml of 0.6 M in toluene, 16.9 mmol). This was stirred for 10 minutes then added to the suspension. The reaction was heated to 70° C. for 1.5 hours. It was then cooled to room temperature, quenched with water, and extracted with ethyl acetate. Purification was performed via silica gel chromatography (0-75% ethyl acetate in hexane) to yield the title compound.

Provenance & Evidence