Isobutyronitrile → HCID 58897024, compound

To a solution of isobutyronitrile (T) (830 mg, 12 mmol, 1 equiv.) in toluene (16 mL) at 0° C., a solution of KHMDS 0.5 M in toluene (26 mL, 13 mmol, 1.05 equiv.) was added. The resulting mixture was warmed to room temperature and stirred for 15 min. This mixture was then added to a solution of 2,6-dichloropyridine (S)(4.39 g, 29.7 mmol, 2.5 equiv.) in toluene (10 mL) and the resulting solution was stirred at room temperature for 1 h. The reaction was quenched with a saturated solution of NH4Cl, followed by aqueous NaHCO3. The crude reaction was diluted in diethyl ether, washed with brine, dried over anhydrous Na2SO4 and the solvent was then removed under reduced pressure. The resulting material was purified by flash chromatography on silica gel, eluting with mixtures of dichloromethane/hexanes (2:1). The title compound U was isolated as a white solid (1.1 g, 51%). 1-(6-chloropyridin-2-yl)cyclopropanecarbonitrile (V), 1-(6-chloropyridin-2-yl)cyclopentanecarbonitrile (W), 1-(6-chloropyridin-2-yl)cyclohexanecarbonitrile (X), and ethyl 2-(6-chloropyridin-2-yl)-2-methylpropanoate (Y) were made following the procedure for 2-(6-chloropyridin-2-yl)-2-methylpropanenitrile (U).

1. stirringthe resulting solution was stirred at room temperature for 1 h
2. customThe reaction was quenched with a saturated solution of NH4Cl
3. customThe crude reaction
4. washwashed with brine
5. dry with materialdried over anhydrous Na2SO4
6. customthe solvent was then removed under reduced pressure
7. customThe resulting material was purified by flash chromatography on silica gel
8. washeluting with mixtures of dichloromethane/hexanes (2:1)

ORD record

ord-82cdae28fa094c73b43485e15c8f822e

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921376B2