[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[NH:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:14]([N:16]([CH2:19][CH2:20]Cl)[CH2:17][CH3:18])[CH3:15].O>CN(C)C=O>[OH2:9].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[N:10][CH2:15][CH2:14][N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[O:9])=[CH:4][CH:3]=1A solution of 4-bromophenyl-methylsulfoximine (10.0 g, 42.7 mmol) in dimethylformamide (50 mL) was added dropwise to a stirring slurry of sodium hydride (2.04 g, 51.2 mmol, 60% oil dispersion washed (3×20 mL) with hexane) which was maintained at 0° C. After stirring for 30 minutes, a solution of diethylaminoethyl chloride (6.58 g, 48.3 mmol) in dimethylformamide (20 mL) was added dropwise. The reaction mixture was warmed at 60° C. for 18 h. The reaction mixture was then cooled to ambient temperature, and 5 mL of water was added. The resulting solution was concentrated in vacuo. The residue was partitioned between 0.1N aqueous HCl (100 mL) and methylene chloride (100 mL). The layers were separated, and the aqueous layer was extracted with methylene chloride (2×50 mL). The aqueous layer was then made basic with 50% aqueous sodium hydroxide, and the resulting slurry was extracted with methylene chloride. These combined organic extracts were washed with saturated sodium chloride, dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed (flash, SiO2, 9:1 methylene chloride:methanol) to give 9.1 g (62%) of clear oil.
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