Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[C:16](B(O)O)[CH:15]=[CH:14][N:13]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CC(O)CC>[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[C:16]([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[CH:6][N:7]=2)[CH:15]=[CH:14][N:13]=1
To a flask containing (6-chloropyridin-3-yl)methanamine 33-2 (375 mg, 2.63 mmol), 2-(trifluoromethyl)pyridin-4-ylboronic acid 33-1 (500 mg, 2.63 mmol), Pd(OAc)2 (34 mg, 0.15 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (124 mg, 0.30 mmol) and potassium phosphate (1.90 g, 9.00 mmol) under argon was added 2-butanol (4 mL). The mixture was stirred at 100° C. for 10 hours. After cooling to room temperature, the mixture was filtered through celite cake. The filtrate was diluted with ethyl acetate, washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 5% methanol containing ˜7N ammonia in dichloromethane to give (2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 33-3 as a yellow solid. MS m/z 254.1 (M+1)
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