Tributylvinyltin → HCID 21931759, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 138 mg (0.048 mmol) 5-methoxy-6-bromo-1,3,3-trimethyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one, 138 mg (0.48 mmol) of tri-n-butyl-vinyltin and 15 mg of bis(triphenylphosphine-palladium(II) chloride in 1 ml of HMPA was heated under nitrogen to 65° C. for 14 hours. The reaction mixture was cooled to room temperature and diluted with water and ethyl acetate. The ethyl acetate solution was washed with water several times. To this ethyl acetate solution was added 1 ml of saturated KF, and the mixture filtered. The filtrate was dried (Na2SO4), evaporated, and the residue chromatographed on silica using 1:1 ethyl acetate/hexanes as the elutant. Appropriate fractions were combined and evaporated to afford 82 mg of 5-methoxy-1,3,3-trimethyl-6-vinyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one. 1H NMR (CDCl3) δ 6.90 (d,d 1H), 5.75 (d, 1H), 5.30 (d, 1H), 3.95 (s, 3H), 3.20 (s, 3H), 1.40 (s, 6H).

Provenance & Evidence