[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:16]4[N:17]=[C:18]([NH2:20])[S:19][C:15]=4[CH:14]=3)[N:10]=[C:4]2[CH:3]=1.[BrH:23].[NH+]1C=CC=CC=1.Br.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.C(OCC)C.C(OCC)(=O)C.O>[Br:23][C:8]1[N:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]2=[N:10][C:9]=1[CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:16]2[N:17]=[C:18]([NH2:20])[S:19][C:15]=2[CH:14]=1
A mixture of 6-[2-(7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-aminobenzothiazole (0.4 g), pyridinium hydrobromide perbromide (0.5 g) and 25% hydrogen bromide-acetic acid (0.1 ml) in acetic acid (4 ml) was stirred at ambient temperature for 1 hour. The reaction mixture was added to a mixture of ethyl acetate and water and the mixture was adjusted to pH 8 with 20% aqueous potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated to give a residue, which was triturarted with a solution of ethyl acetate and diethyl ether to give a precipitate. The precipitate was collected by filtration and dried to give 6-[2-(3-bromo-7-methylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-aminobenzothiazole (0.38 g).
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