6-Butyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione → HCID 19700866, compound

Participants

Reaction Conditions

Reaction Steps

6-(n-Butyl)-pyrrolo[3,4-b]pyridine-5,7-dione (20 g, 98 mmole) was dissolved in toluene (500 mL) and cooled to -65° C. To this mixture was added 3-chlorophenylmagnesium bromide (prepared by heating under reflux 2.5 g magnesium metal, 20 g of 3-chlorobromobenzene and 100 mL of tetrahydrofuran for 1 hour) at such a rate that the temperature of the reaction remain below -40° C. After the addition was complete, the cooling bath was removed and the mixture was allowed to warm to 0° C. The reaction mixture was quenched with aqueous ammonium chloride (25 mL) diluted with ethyl acetate (250 mL) and water (250 mL). After separating the resulting 2 layers, the organic fraction was dried with sodium sulfate (50 g). Filtration, followed by solvent removal gave 7-hydroxy-7-(3-chlorophenyl)-6-(n-butyl)-6,7-dihydropyrrolo[3,4-b]pyridin-5-one as an oil, which was used in the next reaction without further purification.

Provenance & Evidence