Water → (3S)-N,N-dibenzyl-5-pyridin-3-ylchroman-3-amine

Participants

Reaction Steps

Palladium-tetrakis(triphenylphosphine) (48 mg, 0.042 mmol) and (3S)-3-(dibenzylamino) -3,4-dihydro-2H-chromen-5-yl trifluoromethanesulfonate (200 mg, 0.42 mmol) in dioxane (4 mL) were added to 3-(tri-N-butylstannyl)pyridine (232 mg, 0.63 mmol) under an atmosphere of argon and the resulting reaction mixture was irradiated in a microwave at 120-140° C. for 1.5 h. More palladium-tetrakis(triphenylphosphine) (48 mg, 0.042 mmol) was added and the irradiation was continued at 140° C. for 1 h. Water (20 mL) was added and the mixture was extracted with ethyl acetate. The organic phases was dried over sodium sulfate, the solvent was evaporated in vacuo and the residue purified by column chromatography, using a gradient of ethyl acetate in heptanes as the eluent, gave 63 mg (74%) of the title compound: MS (ES) m/z 407[M+H+].

Provenance & Evidence