Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:18])=[N:7][N:8]2[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)=[CH:4][CH:3]=1.N1CCCCC1.[C:25]([Si:27]([CH3:30])([CH3:29])[CH3:28])#[CH:26]>[Cu]I>[CH3:18][C:6]1[C:5]2[C:9](=[CH:10][C:2]([C:26]#[C:25][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:3][CH:4]=2)[N:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=2)[N:7]=1To a pressure tube was added 4-(6-bromo-3-methylindazol-1-yl)pyrimidin-2-amine (0.5 g, 1.64 mmol), piperidine (3.5 mL) tetrakis(triphenylphosphine)palladium (113.98 mg, 0.1 mmol), copper(I) iodide (18.79 mg, 0.1 mmol) and ethynyl(trimethyl)silane (0.47 ml, 3.29 mmol). The mixture was purged with nitrogen for 2 minutes and then stirred at 65° C. for 1.5 hr. The reaction mixture was concentrated in vacuo, DCM (5 mL) was added and the concentration repeated (×2). The mixture was purified by column chromatography (Biotage, 3-8% MeOH gradient in DCM) to give the title intermediate as a white solid (116 mg): 1H NMR (250 MHz, DMSO) delta 0.28 (9H, s), 2.57 (3H, s), 7.03 (3H, d, J=5.5), 7.38 (1H, d, J=8.2), 7.84 (1H, d, J=8.2), 8.26 (1H, d, J=5.5), 8.90 (1H, s); LC-MS: m/z=+322.50 (M+H)+.
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