[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:9]([O:8][C:7]1[C:2]([Br:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1A mixture of 2-bromo-pyridine-3-ol (50.4 g, 0.29 mol), benzyl bromide (45.5 g, 0.28 mol) and potassium carbonate (52 g, 0.38 mol) in dry N,N-dimethylformamide (DMF; 300 mL) was heated at 110° C. for 30 minutes. The mixture was filtered through a pad of Celite®, the solvent was removed under reduced pressure and the black residue was taken up between ice cold 0.5 M aqueous NaOH and EtOAc. The organic phase was washed twice with brine, dried (MgSO4), and concentrated under reduced pressure to yield 69.6 g (93%) of the title compound as a brown oil. HRMS m/z calcd for C12H10BrNO (M)+ 263.9946. found 263.9939. *Previously described in J. Med. Chem. 1996, 39, 5267–5275.
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