Methyl iodide → 5-methoxy-1-methyl-1H-indole

To a solution of 5-methoxyindole (200 mg, 1.36 mmol) in 1.5 mL of dry N,N-dimethylformamide was added sodium hydride (55%, 66 mg, 1.5 mmol) at 0° C. After the reaction mixture was stirred at the same temperature for 30 min, methyl iodide (0.10 mL, 1.6 mmol) was added with additional stirring at room temperature overnight. After the reaction mixture was quenched with water (5 mL) at 0° C., the solution was extracted with diethyl ether (20 mL) twice. The combined extracts were washed with brine (5 mL), and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain 5-methoxy-1-methylindole (182 mg, 83%).

1. stirringwith additional stirring at room temperature overnight
2. customAfter the reaction mixture was quenched with water (5 mL) at 0° C.
3. extractionthe solution was extracted with diethyl ether (20 mL) twice
4. washThe combined extracts were washed with brine (5 mL)
5. dry with materialdried over MgSO4
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated in vacuo
8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

ORD record

ord-52d5171230164757ba8557117c36b7f6

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08686024B2