Tetraethyltin → HCID 21873607, compound

Participants

Reaction Steps

Methyl 7-bromo-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate (Example 304b) (2.00 g, 6.6 mmol), tetraethyltin (3.17 mL, 16 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.12 g, 1.6 mmol) in dimethylformamide (40 mL) were heated at 120° C. for 24 h. The mixture was filtered through Kieselguhr, washed through with ethyl acetate and evaporated. Chromatography on silica gel (20-50% ethyl acetate/petroleum ether) gave a mixture of the 7-ethyl and 7-vinyl compounds (0.29 g). This mixture was hydrogenated in methanol/ethyl acetate (2:1, 60 mL) over 10% palladium on carbon (60 mg) (1 atmosphere, room temperature) for 24 h. Filtration and evaporation of solvent gave the product (0.28 g).

Provenance & Evidence