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

Participants

Reaction Steps

To a solution of 2,5-dibromopyridine (5.0 g, 21 mmol) and 2-methylpropanenitrile (1.6 g, 23 mmol) in toluene (50 mL) under nitrogen was added NaHMDS (12 mL, 23 mmol, 2.0M in THF) dropwise at 0° C. The resulting solution was stirred at ambient temperature overnight before the addition of saturated aqueous NH4Cl (20 mL). The resulting mixture was extracted with EtOAc (3×30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 1-3% EtOAc/hexane) to afford the title compound as a light yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.65 (s, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.51 (d, J=8.7 Hz, 1H), 1.75 (s, 6H). MS ESI [M+H]+ m/z 225.227.

Provenance & Evidence