Cl[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][S:5]1(=[O:10])=[O:9].[Br:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[N:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[Br:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14]([O:18][CH2:2][CH2:3][N:4]2[CH2:8][CH2:7][CH2:6][S:5]2(=[O:10])=[O:9])[CH:13]=1
To a solution of 2-(2-chloro-ethyl)-isothiazolidine-1,1-dioxide (0.046 g, 0.253 mmol) and 5-bromopyridin-3-ol (0.04 g, 0.230 mmol) in DMF (1 mL) was added K2CO3 (0.064 g, 0.46 mmol), followed by KI (0.008 g, 0.046 mmol) and the reaction mixture was heated to 60° C. and stirred over night. The mixture was diluted with EtOAc, poured into a sat. NaHCO3 solution (5 mL) and the aqueous layer was extracted with EtOAc (2×10 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.015 g, 20%) as a yellow oil which was used with no further purification. MS: 321.3 and 323.2 (M+H+).
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