Triethylamine → 3-Bromopyridine-2-carbonitrile

Temperature

100 °C

3-Bromo-pyridine 1-oxide (9.4 g, 54 mmol) is dissolved in acetonitrile (60 mL) and triethylamine (15 mL) is added followed by trimethylsilyl cyanide (21.7 mL, 163 mmol). The mixture is heated to 100° C. and stirred for 16 h. The mixture is cooled to 0° C., poured into 250 mL of 5 M aqueous NaOH, and extracted with dichloromethane. The combined extracts are washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting material is purified using flash chromatography (Biotage® Si65M, 20% ethyl acetate/hexane) to yield 7.8 g (79%) of the title compound as a yellow solid. GCMS m/e 182, 184 [M]−.

1. temperatureThe mixture is cooled to 0° C.
2. extractionextracted with dichloromethane
3. washThe combined extracts are washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe resulting material is purified

ORD record

ord-fb2b7ffee1274ddfa8ee8a9111628aa8

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101760B2