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

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 2 N solution of NaHMDS in THF (12 mL, 23 mmol) dropwise at 0° C. The resulting solution was stirred at ambient temperature overnight before the addition of saturated aqueous NH4Cl solution (20 mL). The resulting mixture was extracted with ethyl acetate (3×30 mL). All the organic solution was dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography with 1-3% ethyl acetate in hexane to afford the title compound as a light yellow solid. MS ESI [M+H]+ m/z 225, 227; 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).

1. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
2. dry with materialAll the organic solution was dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude residue was purified by flash column chromatography with 1-3% ethyl acetate in hexane

ORD record

ord-9da10edd2c894f5f883e69cebda57fba

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394282B2