[CH:1](=[N:23][OH:24])[C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][N:16]=4)[CH:10]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.ClN1C(=O)C[CH2:28][C:27]1=O.C(Br)=C.C(N(CC)CC)C>CN(C=O)C.O>[O:24]1[CH:28]=[CH:27][C:1]([C:2]2[CH:22]=[CH:21][C:5]3[N:6]([C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([C:15]5[CH:20]=[CH:19][N:18]=[CH:17][N:16]=5)[CH:10]=4)[CH:7]=[N:8][C:4]=3[CH:3]=2)=[N:23]1A mixture of 42a (2.1 g) and N-chlorsuccinimide (1.1 g, 1.2 equivalents) in DMF (100 ml) was stirred under argon at 60° C. for 0.5 hours. Vinyl bromide (25 ml) was added to the reaction mixture under ice-cooling, and thereafter triethylamine (4.8 ml, 5 equivalents) in 15 ml DMF was added dropwise over one hour. The mixture was stirred at 0° C. for 3 hours and at room temperature overnight. The mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried, and concentrated under reduced pressure. The residue was purified by column-chromatography on silica gel using a mixture of CH2Cl2 and methanol (30:1) as the eluent to give 5-(3-isoxazolyl)-1-(3-(4-pyrimidinyl)phenyl)benzimidazole (1.5 g, 64%).M.p. 214-215° C.
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