2-(Boc-amino)-5-bromopyridine → Tert-butyl 5-tert-butylpyridin-2-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a mixture of anhydrous CuCN (2.7 g, 30.4 mmol) in 100 mL of THF was added a solution of tert-butylmagnesium chloride (30.4 mL, 60.2 mmol, 2M solution in THF) under N2 at −78° C. After 20 minutes, tert-butyl 5-bromopyridin-2-ylcarbamate (2.1 g, 7.6 mmol, Aldrich) was added. The reaction mixture was stirred for 2 hours at −78° C. and then at room temperature for 12 hours. The mixture was quenched with saturated aqueous NH4OH and basified to pH 7 with 20% aqueous NaOH. The solid was filtered through a pad of Celite. The filtrate was extracted with ether and washed with water. The organic extract was dried over MgSO4 and concentrated. Purification by column chromatography (SiO2: 0-15% hexanes/ethyl acetate gradient) afforded 0.4 g of the title compound. MS (ESI+) m/z 251 (M+H)+.

Provenance & Evidence