[CH3:1][S:2]([CH2:5][CH2:6][CH2:7][OH:8])(=[O:4])=[O:3].[H-].[Na+].[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18]Br)[CH:17]=1.[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O.O>[Br:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([CH2:18][O:8][CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:17]=13-Methanesulfonyl-propan-1-ol (69 mg, 0.50 mmol) is dissolved in 2.0 mL of DMF and 60% sodium hydride (20 mg, 0.50 mmol) is added at 0° C. The mixture is stirred for 15 min and 3-bromo-5-bromomethyl-pyridine (50 mg, 0.20 mmol) is added. The mixture is stirred for 2 hrs and saturated aqueous NH4Cl solution (3 mL) is added along with water (10 mL) and EtOAc (10 mL). The mixture is stirred for 10 min and the aqueous layer is separated and extracted with EtOAc (2×15 ml). The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 61 mg of 3-bromo-5-(3-methanesulfonyl-propoxymethyl)-pyridine.
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