[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([C:9]#[C:10][CH:11]([CH3:13])[CH3:12])=[CH:4][N:3]=1.CC([O-])(C)C.[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN1C(=O)CCC1.C1COCC1.CN(C=O)C>[CH2:20]([N:8]1[C:6]2[CH:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=2[CH:9]=[C:10]1[CH:11]([CH3:13])[CH3:12])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1To a solution of 2-chloro-5-(3-methylbut-1-ynyl)pyridin-4-amine (Compound 12, 0.82 g, 4.2 mmol) in NMP (10 ml) was added KOtBu (2.40 g, 21 mmol). The mixture was stirred at 160° C. for 6 h and was cooled to room temperature, diluted with THF (10 ml) and DMF (15 ml). Benzyl bromide (0.50 ml, 4.2 mmol) was added. The mixture was stirred at room temperature for 16 h and was quenched with H2O, extracted with EtOAc (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a white solid.
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