Methyl iodide → 6-methoxy-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[NH:1]1[C:5]2=[N:6][C:7]([OH:10])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[C:11](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH3:11][O:10][C:7]1[N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]2=[CH:9][CH:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1H-pyrrolo[2,3-b]pyridin-6-ol (1.52 g, 11.4 mmol) and potassium carbonate (7.86 g, 57 mmol) in acetone (100 mL) was stirred under nitrogen at room temperature for 1 h. Iodomethane (2.6 g, 18.2 mmol) was added and the resulting mixture stirred at 56° C. for 12 h. The mixture was filtered, and the filtrate was concentrated to half its volume, diluted with water, and extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and evaporated. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 20% ethyl acetate/hexanes) to afford 6-methoxy-1H-pyrrolo[2,3-b]pyridine (0.5 g, 30%): LC/MS m/e calcd for C8H8N2O [M+H]+ 149.17, observed 149.1.