[OH:1][C:2]1[C:3]2[N:4]([CH:8]=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[K+]>CN1CCCC1=O.[Cu]>[CH3:11][C:9]1[N:10]=[C:3]2[C:2]([O:1][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=[CH:5][N:4]2[CH:8]=1A mixture of 8-hydroxy-2-methylimidazo[1,2-a]pyridine (14.8 g), bromobenzene (15.7 g), copper powder (1.0 g) and powdered potassium hydroxide (5.6 g) in N-methyl pyrrolidone was heated under reflux for 4 hrs. The solvent was removed by distillation and the residue suspended in dichloromethane, washed with 10% sodium hydroxide solution and the dichloromethane was evaporated to give 2-methyl-8-phenoxyimidazo[1,2-a]pyridine. Treatment of this compound in accordance with Examples 10 and 11 yields the desired product.
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