Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1>[CH:10]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=2)[CH2:12][CH2:11]1To a solution of 4-bromopicolinonitrile (0.2 g, 1.1 mmol) in tetrahydrofuran were added cyclopropyl boronic acid (0.093 g, 1.1 mmol), and potassium phosphate tribasic (0.694 g, 3.2 mmol). The resulting reaction mixture was degassed with nitrogen for 10 minutes and then added Pd(OAc)2 and S-phos were added. The reaction mixture was heated at reflux for 16 h, then was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified via flash chromatography (10% ethyl acetate in petroleum ether) to afford 4-cyclopropylpicolinonitrile (0.1 g, 70%). MS (ES+APCI) (M+H) 145.2; LCMS retention time 3.02 min (Method J).
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