[Br:1][C:2]1[C:3]([CH3:10])=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:12]([F:23])([F:22])[F:11])[CH:18]=2)[C:5]([NH2:8])=[N:6][CH:7]=15-Bromo-3-iodo-4-methyl-pyridin-2-ylamine (20.0 g, 63.9 mmol) and 3-(trifluoromethyl)benzene boronic acid (12.73 g, 67.0 mmol) were mixed with sodium carbonate (2 M, 160 mL, 320 mmol), toluene (570 mL) and IMS (190 mL) and degassed. 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane (3.13 g, 36.83 mmol) was added and the reaction mixture was degassed again before heating to reflux for 2 hrs. A second reaction was carried on 1.08 times the scale. The two batches were combined and the solvent was removed in vacuo and the resulting mixture was partitioned between DCM and water. The organic phase was separated and was washed with water, dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography through a pad of silica, eluting with a gradient of 5-30% EtOAc in cyclohexane to give the title compound as a beige solid (34.6 g).
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