Water → (+/-)-2a,6-Dimethyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one

Participants

Reaction Steps

A mixture of (±)-6-bromo-2a-methyl-1,2,2a,5-tetrahydropyrrolo[4,3,2-de]quinolin-4(3H)-one from Step B (48 mg, 0.18 mmol), tetrakis(triphenylphosphine)palladium(0) (22 mg, 0.019 mmol), potassium carbonate (75 mg, 0.54 mmol), and trimethylboroxine (0.126 mL of a 50 wt. % solution in THF, 0.50 mmol) in 1,4-dioxane (0.9 mL) and H2O (0.1 mL) was heated at 120° C. in a microwave reactor for 40 min. The cooled reaction mixture was quenched with H2O (5 mL) and extracted with EtOAc (20 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 CH2Cl2:MeOH—100:0 to 90:10, to give the title compound. MS: m/z=203 (M+1).

Provenance & Evidence