C(O)(C)(C)C.C(NCC)C.[Cl:11][C:12]1[N:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=1.Br[CH2:22][C:23]([C:25]1[CH:26]=[N:27][C:28]([Cl:31])=[CH:29][CH:30]=1)=[O:24].OS(O)(=O)=O>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[Cl:11][C:12]1[N:17]=[CH:16][C:15]([C:18](=[O:20])[CH2:19][CH2:22][C:23]([C:25]2[CH:26]=[N:27][C:28]([Cl:31])=[CH:29][CH:30]=2)=[O:24])=[CH:14][CH:13]=1The zinc chloride (3.04 g, 22.82 mmol), tert-butyl alcohol (1.576 mL, 16.71 mmol) and diethylamine (1.731 mL, 16.71 mmol) were combined in benzene (12 mL). The resulting slurry was stirred at room temperature for 2 hours until all solid dissolved. To this slurry was added 1-(6-chloropyridin-3-yl)ethanone (2.60 g, 16.71 mmol; reference: Bioorganic & Medicinal Chemistry Letters, 1998, 8, 3087-3092), followed by 2-bromo-1-(6-chloropyridin-3-yl)ethanone (2.61 g, 11.14 mmol; reference: Bioorganic & Medicinal Chemistry Letters, 1998, 8, 3087-3092). The resulting clear yellow solution was stirred at room temperature for 88 hours. The thick reaction mixture was treated with 5% H2SO4 (10 mL), stirred for 30 minutes, filtered and dried to give the title compound (2.91 g, 85%) as a solid.
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