[Br:1][C:2]1[C:3]([OH:9])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[H-].[Na+].[Br-].[Li+].I[CH3:15]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[C:3](=[O:9])[N:4]([CH3:15])[C:5]([CH3:8])=[CH:6][CH:7]=13-Bromo-6-methylpyridine-2-ol (2 g, 10.6 mmol) was taken up in THF and stirred. Sodium hydride (60% in oil 510 mg, 12.7 mmol) was added portion wise then stirred 30 minutes. Lithium bromide (1.85 g, 21.2 mmol) was added and stirred for 1 hour. Then iodomethane (1.32 mL, 21.2 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was diluted with DCM and washed with 1N NaOH. The DCM layer was dried over magnesium sulfate, filtered and dried in vacuo to afford 1.19 g product carried on to next step as is. LRMS (ESI) m/z 202/204 [(M+H)]+, calc'd for C7H8BrNO: 202.05.
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