[OH:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[CH:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:17]I>CN(C)C=O>[CH3:17][O:1][CH2:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[CH:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1A solution of 6-hydroxymethyl-1-(2-propyl)indole (0.214 g, 1.13 mmole) in 2 mL of anhydrous N,N-dimethylformamide was added dropwise to a slurry of 95% NaH (35.2 mg, 1.36 mmole) in 6 mL of anhydrous N,N-dimethylformamide at 0° C. under argon and the reaction mixture was stirred at 0° C. for 1 h followed by addition of methyl iodide (84.7 mL, 1.356 mmole). The reaction was then stirred at 20° C. under argon for 17 h. It was poured into ice-water (50 mL) and extracted with ethyl acetate. The ethyl acetate layers were dried over anhydrous magnesium sulfate and evaporated. Purification by flash chromatography using ethyl acetate (2-5%)/hexanes gave 107 mg of 6-methoxymethyl-1-(2-p-ropyl) indole.
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