Methyl iodide → HCID 136352239, compound

Participants

Reaction Conditions

Reaction Steps

A 70/30 mixture of 2-(1H-Pyrrolo[2,3-c]pyridin-5-yl)-chromen-4-one O-tert-butyl-oxime and 2-(1-Hydroxy-1H-pyrrolo[2,3-c]pyridin-5-yl)-chromen-4-one O-tert-butyl-oxime (77 mg) in dimethylformamide (5 ml) was cooled to 0° C. and treated with sodium hydride (60% in mineral oil, 10 mg, 0.25 mmol) and stirred at room temperature for 1 hour. The solution was cooled down to 0° C. and treated with iodomethane (16 μl, 0.25 mmol). The solution was slowly warmed up to room temperature during 1 hour and poured into brine, extracted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated to dryness. The crude mixture of 2-(1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)-chromen-4-one O-tert-butyl-oxime and 2-(1-methoxy-1H-pyrrolo[2,3-c]pyridin-5-yl)-chromen-4-one O-tert-butyl-oxime was treated with titanium tetrachloride (0.70 mmol) in dichloromethane (7.5 ml) (method D) to yield separately after purification by preparative HPLC (gradient 65-50% Water/Methanol+0.05% trifluoroacetic acid), 2-(1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)-chromen-4-one oxime (example 77, 17 mg) and 2-(1-methoxy-1H-pyrrolo[2,3-c]pyridin-5-yl)-chromen-4-one oxime (example 78, 12 mg) as yellow solids.

Provenance & Evidence