Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+].CO[CH2:24][CH2:25]OC>O>[CH:24]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]#[N:15])=[CH2:25]To a solution of 4-chloro-6-(methyloxy)-3-quinolinecarbonitrile (1.1 g, 5.03 mmol), potassium carbonate (0.76 g, 5.53 mmol), tetrakis-triphenylphosphine (120 mg, 0.10 mmol) in DME (30 mL) and H2O (10 mL) was added 2,4,6-trivinylcycloborane-pyridine complex (1.33 g, 5.53 mmol). After stirring for 5 hours at 85° C. the reaction contents was concentrated and the product purified by chromatography on silica gel (hexanes/EtOAc, 4:1) to give a light brown solid (0.9 g, 86%): LC/MS (ES) m/e 211 (M+H)+.
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