Br[C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH2:27][CH3:28])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19]C(OC(C)(C)C)=O)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[Cu](C#N)[C:30]#[N:31].O.N>CN(C)C=O>[C:30]([C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH2:27][CH3:28])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1)#[N:31]To a solution of 4-(3-bromophenyl)-5-[2-(tert-butoxycarbonylamino)-4-pyridyl]-2-ethyl-1,3-thiazole (0.5 g, 1.1 mmol) in N,N-dimethylformamide (10 mL) was added copper cyanide (0.25 g, 1.6 mmol), and the mixture was stirred for 20 hours at 150° C. under argon atmosphere. Into the reaction mixture was poured ammonia water, and the deposit was removed, then, extracted with ethyl acetate. The extracts were washed with water, then, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1) to obtain a crystal. This crystal was washed with hexane-ethyl acetate to obtain a title compound (0.19 g, yield 57%).
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