[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:10][OH:11])[CH:7]=[N:8][CH:9]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].O>O1CCCC1>[CH3:12][S:13]([O:11][CH2:10][C:6]1[CH:7]=[N:8][CH:9]=[C:4]([Br:3])[CH:5]=1)(=[O:15])=[O:14]To a cooled (0° C.) suspension of sodium hydride (60% dispersion in mineral oil, 0.064 g, 1.60 mmol) in tetrahydrofuran (5 mL) was added a solution of (5-bromopyridin-3-yl)methanol (0.200 g, 1.06 mmol) in tetrahydrofuran (5 mL). After stirring for 1 hour, methanesulfonyl chloride (0.099 mL, 1.28 mmol) was added. The reaction was then warmed to room temperature and stirred until complete. The reaction was then poured into water and extracted with ethyl acetate. The organic extracts were combined, washed with water and saturated aqueous sodium chloride solution, dried, filtered, and concentrated under reduced pressure to provide the title compound: LCMS m/z 267.86 [M+2+H]+.
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