Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:14]=[N:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:17]=2)[N:3]=1.[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH:33]([CH3:37])[C:34]([NH2:36])=[O:35])#[CH:26].F[B-](F)(F)F.CCN(C(C)C)C(C)C>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[NH2:36][C:34](=[O:35])[CH:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:25]#[C:26][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:14]=[N:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:17]=2)[N:3]=1)[CH3:37]A degassed mixture of tert-butyl 4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-1H-pyrazole-1-carboxylate A61 (0.373 g, 1.03 mmol), 2-(2-ethynylphenyl)propanamide K7 (0.452 g, 2.40 mmol), PdCl2(PPh3)2 (0.015 g, 0.02 mmol), t-Bu3PH.BF4 (0.011 g, 0.038 mmol) and CuI (0.007 g, 0.04 mmol) in 1,4-dioxane (6.0 mL) and DIPEA (0.90 mL, 5.2 mmol) was heated in the microwave at 100° C. for 30 minutes. The mixture was concentrated under reduced pressure and purified using silica gel column chromatography (0-100% EtOAc in petroleum benzine 40-60° C.) to give the title compound A62 (0.309 g, 58%). LCMS-D: rt 3.533 min; m/z 502.2 499.2 [M−H]−.
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