Sodium Cyanide → 2-(5,6-Dichloropyridin-2-yl)acetonitrile

Temperature

100 °C

To a solution of 6-(bromomethyl)-2,3-dichloropyridine (Preparation 60, 2.90 g, 3.13 mmol) in IMS (20 mL) and water (15 mL) was added NaCN (552 mg, 11.3 mmol). The reaction was heated to 100° C. for 1 hour before cooling to room temperature and quenching with saturated aqueous NaHCO3 solution (50 mL). The mixture was extracted with DCM (3×50 mL) and the organic layers combined, dried over MgSO4 and concentrated in vacuo. The residue was purified using reverse phase column chromatography eluting with 0-100% MeCN in water with 0.1% formic acid to afford the title compound (341 mg, 15% over two steps).

1. temperaturebefore cooling to room temperature
2. customquenching with saturated aqueous NaHCO3 solution (50 mL)
3. extractionThe mixture was extracted with DCM (3×50 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. customThe residue was purified
7. washeluting with 0-100% MeCN in water with 0.1% formic acid

ORD record

ord-675af7e2f62140bcaeff8646c9c52124

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328096B2