(+/-)-6-Bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one → (+/-)-2a-Methyl-4-oxo-1,2,2a,3,4,5-hexahydropyrrolo[4,3,2-de]quinoline-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-6-bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one (53 mg, 0.20 mmol, described in Intermediate 47), tetrakis(triphenylphosphine)palladium(0) (48 mg, 0.042 mmol), and copper(I) cyanide (27 mg, 0.30 mmol) in DMF (2 mL) was heated at 150° C. for 3 h. The cooled reaction mixture was quenched with aqueous NaHCO3 (10 mL) and extracted with EtOAc (30 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—60:40 to 0:100, to give the title compound in sufficient purity for use in the next step. MS: m/z=214 (M+1).

Provenance & Evidence