[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([OH:18])[CH:11]=3)=[N:7][C:6]=2[CH:19]=1.[C:20]([O-:23])([O-])=O.[K+].[K+].Br[CH2:27]CCBr>CC#N>[CH3:20][O:23][C:11]1[C:12]([O:18][CH3:27])=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:19][C:6]=2[N:7]=1To a solution of 5-fluoro-2-(3-hydroxy-4-methoxyphenyl)benzothiazole 5 (0.15 g, 0.55 mmol) in CH3CN (30 ml) were added K2CO3 (0.11 g, 0.82 mmol) and 1,3-dibromopropane (0.28 ml, 2.74 mmol), and the mixture was heated under reflux at 80° C. for 24 hours. The reaction mixture was allowed to cool at room temperature and then concentrated in vacuum. The residue was taken up with CHCl3 (30 ml), and the CHCl3 layer was washed with 0.2N NaOH aq (30 ml×2), then dried and concentrated in vacuum. The residue was purified by column chromatography on silica gel (chloroform), followed by recrystallisation from ethanol/water to give a white solid.
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