2-(2-bromopyridin-3-yl)acetonitrile

A solution of (2-bromopyridin-3-yl) methyl methanesulfonate 2 (200 mg, 0.75 mmol) and NaCN (0.18 g, 3.75 mmol) in DMSO (2 mL) was stirred overnight at room temperature. Ethylacetate (10 mL) was then added. The resulting solution was washed with water (3X10 mL) then extracted with ethylacetate (3X10 mL). The organic layer was dried over MgSO4 then evaporated to yield a brown oil which was filtered through a short pad of silica with diethylether to give compound 3 as white crystals (95percent).To a -60 °C mixture of t-BuOK (5.92 g, 52.76 mmol) in 1, 2-dimethoxyethane (50 mL)was added a solution of 2-tosylacetonitrile (5.08 g, 26.02 mmol) in 1, 2-dimethoxyethane (20 mL)dropwise. To the resulting mixture was added a solution of 2-bromonicotinaldehyde (4.81 g, 25.86 mmol) in 1 , 2-dimethoxyethane (20 mL) dropwise at -60 °C. After stirring for 1 h at thistemperature, MeOH was added (50 mL), the resulting mixture was allowed to warm to RT, stirred for 1 h and warmed to 85 °C, stirred for another lh. After cooling to RT, the volatiles was removedunder reduced pressure, diluted with brine (200 mL) and extracted with EA (3 x 150 mL). Thecombined organic layers were dried over anhydrous Na2504, filtered and concentrated underreduced pressure. The residue was purified by silica chromatography (eluting with EA: Hex = 1:10, v/v) to give 2-(2-bromopyridin-3-yl)acetonitrile (2.21 g). MS: m/z 197 (M+H) .

Molecular Weight:197.03
XLogP3:1.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:36.7
Heavy Atom Count:10
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes