Methyl iodide → N-methyl-7-azaindole

HRID 53165

Reaction equation

[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].I[CH3:13]>CN(C)C=O>[CH3:13][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

Pyrrolo[2,3-b]pyridine (2.00 g, 16.93 mmol) is dissolved in dimethylformamide (15.0 ml) under an argon atmosphere. Sodium hydride (60% in oil) (0.96 g, 40.0 mmol, 1.5 equiv.) is added at 0° C. over a period of 30 minutes. After 30 minutes' stirring at 0° C., iodomethane (1.49 ml, 24.02 mmol, 1.5 equiv.) is added dropwise. After returning to room temperature, the reaction mixture is stirred for 1 hour. The dimethylformamide is evaporated off under reduced pressure, and the product is taken up in water and extracted with dichloromethane. Purification on a silica column (petroleum ether/ethyl acetate 7/3) allows isolation of the title compound in the form of an oil in a yield of 99%. ##STR31##

Workup

customAfter returning to room temperature
stirringthe reaction mixture is stirred for 1 hour
customThe dimethylformamide is evaporated off under reduced pressure
extractionextracted with dichloromethane
customPurification on a silica column (petroleum ether/ethyl acetate 7/3)

Sources & evidence

ORD record: ord-f98ed61670bb41d79b57c957601641d5
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618819

Linked notes

Loading…