[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:3]=1.[S:11](Cl)([CH3:14])(=[O:13])=[O:12]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:14][S:11]([O:10][CH:8]([C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]=1)[CH3:9])(=[O:13])=[O:12]A stirring solution of the 1-(4-bromopyridin-2-yl)ethanol (3.72 g, 18.41 mmol and DMAP (4.5 g, 36.82 mmol) in 75 mL of dichloromethane was cooled to 0° C. To it was added mesyl chloride (1.71 mL, 22.09 mmol) dropwise. The mixture was stirred at 0° C. for 10 minutes, then warmed to room temperature and stirred for 15 min. The reaction was quenched with 50 mL ice water, the layers were separated, and the aqueous layer was extracted with dichloromethane (50 mL). The organics were combined, washed with water and brine, dried over Na2SO4, and purified by column chromatography (gradient 0 to 45% EtOAc/hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.40 (d, J=5.3 Hz, 1H), 7.64 (d, J=1.6 Hz, 1H), 7.45 (dd, J=5.3, 1.8 Hz, 1H), 5.75 (q, J=6.6 Hz, 1H), 3.00 (s, 3H), 1.75 (d, J=6.6 Hz, 3H).
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