Tri(butyl)vinyltin → HCID 90281270, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (207 mg, 0.5 mmol), tributylvinyl tin (175 μL, 0.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (29 mg, 0.025 mmol) were combined in 10 mL of DMF, and the mixture was heated to 85° C. overnight. The reaction was allowed to cool to ambient temperature and was partitioned between ethyl acetate and water. The organic layer was separated and washed with 5% aqueous LiCl and brine. The organic layer was then dried over MgSO4, filtered and concentrated to afford crude product which was purified by RP HPLC eluting with acetonitrile and water to afford 120 mg of tert-butyl 3-(2-ethoxy-2-oxoethyl)-5-methoxy-2-vinyl-1H-pyrrolo[3,2-b]pyridine-1-carboxylate. MS (m/z): 361.2 [M+H]+; HPLC retention time 4.69 min (5-99% acetonitrile:water with 0.05% formic acid).

Provenance & Evidence