[NH2:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]\[C:10]2[CH:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1To a mixture of tert-butyl {2-[(3-aminophenyl)ethynyl]pyridin-4-yl}carbamate (430 mg, 1.4 mmol) in methanol (15 mL) was added 10% palladium on carbon (150 mg, 0.14 mmol) and hydrogenated at 60 psi for 20 hours. After filtration and concentration, the crude residue was purified by silica gel column chromatography to give the desired product (160 mg, 37%). LCMS for C18H22N3O2 (M+H)+: m/z=312.1
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