Potassium Carbonate → 2-Bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine

Reaction equation

[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=1>CN(C=O)C>[Br:1][C:2]1[C:7]([O:8][CH2:17][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Procedure

A mixture of 2-bromo-3-pyridinol (commercially available, e.g. from Aldrich) (2.9 g) and potassium carbonate (6.94 g) in DMF (25 ml) was stirred for 20 min before adding 2-(chloromethyl)-4-methylpyridine hydrochloride (for preparation see WO 2008/141011) (3 g). This was stirred at room temperature overnight. The reaction mixture was poured into ice/water and the solid formed was collected by filtration, washed with hexane and dried to give the title compound, 2.87 g (61%).