[F:1][C:2]1[CH:7]=[C:6](B(O)O)[CH:5]=[CH:4][N:3]=1.Cl[C:12]1[N:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]1[CH:7]=[C:6]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][NH2:19])=[CH:16][N:17]=2)[CH:5]=[CH:4][N:3]=1
A mixture of (2-fluoropyridin-4-yl)boronic acid 24-1 (200 mg, 1.42 mmol), (6-chloropyridin-3-yl)methanamine 18-1 (142 mg, 1.00 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (41 mg, 0.1 mmol) and K3PO4 (424 mg, 2.00 mmol) in 2-butanol (1 mL) was stirred at 100° C. under argon overnight. After cooling to room temperature, the mixture was filtered through celite (washed with ethyl acetate), concentrated by rotavap and the residue subjected to silica gel column chromatography with 7% ammonia-saturated methanol in dichloromethane as eluent to give (2′-fluoro-[2,4′-bipyridin]-5-yl)methanamine 24-2 as an oil.
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