Potassium Hydroxide → HCID 57891763, compound

Participants

Reaction Steps

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo-[2,3-b]pyridine, 1, (50 mg, 0.20 mmol) was dissolved in methylene chloride (4 mL). Aqueous potassium hydroxide (50% wt/vol, 300 μL) and tetrabutylammonium hydrogen sulfate (2 mg, 0.007 mmol) were added. The reaction mixture was stirred for 10 minutes at room temperature. Into the reaction was added 8-quinoline-sulfonyl chloride (48 mg, 0.21 mmol) and the reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated and the residue was washed with brine and ethyl acetate. The organic portion was dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by preparative TLC (75% ethyl acetate:hexanes). The product was eluted from the silica with ethyl acetate and filtration. The filtrate was concentrated to provide 7 (14 mg, 16%). MS(ESI) [M+H+]+=445.9.

Provenance & Evidence