Cl.Cl[C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][C:4]=1[CH3:11].[F:12][C:13]1[CH:18]=[C:17](B(O)O)[CH:16]=[CH:15][N:14]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[F:12][C:13]1[CH:18]=[C:17]([C:3]2[C:4]([CH3:11])=[CH:5][C:6]([CH2:9][NH2:10])=[CH:7][N:8]=2)[CH:16]=[CH:15][N:14]=1
To a reaction vial was added (6-chloro-5-methylpyridin-3-yl)methanamine HCl salt 30-4 (738 mg, 3.8 mmol), 2-fluoropyridin-4-ylboronic acid 30-5 (800 mg, 5.7 mmol), Pd(OAc)2 (106 mg, 0.47 mmol), S-Phos (194 mg, 0.47 mmol) and K3PO4 (2.0 g, 9.5 mmol). The vial was evacuated and backfilled with nitrogen, and 2-butanol (5 mL) was added via syringe. The reaction was stirred at room temperature for 10 mins and then 100° C. for 3 hours. After cooling to room temperature, the reaction mixture was partitioned between DCM and H2O, and extracted with DCM three times. The organic phase was combined and dried. The crude product was purified by silica gel flash chromatography, eluted with 10% methanol in DCM to give (2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)methanamine 30-5. MS m/z 218.2 (M+1).
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