Acetonitrile → HCID 86747806, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl (S)-10-bromo-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate (U.S. Pat. No. 4,839,355, Example 5f) (3.50 g), 2.97 g of 4-(trimethylstannyl)pyridine and 0.155 g of dichlorobis(triphenylphosphine)palladium were combined in a Parr apparatus in 200 ml of absolute ethyl alcohol and the mixture under nitrogen was heated at 150° C. for 41/2 hours, allowed to cool slowly and concentrated in vacuo. The concentrate was taken up in chloroform and residues were removed by filtration. The filtrate was extracted with sufficient 1M hydrochloric acid to extract all the product and the aqueous extract was poured onto ice and saturated sodium acetate was added. The resulting mixture was extracted with chloroform and the chloroform extract was washed with brine followed by sodium bicarbonate, dried over magnesium sulfate and concentrated to give, after recrystallization from acetonitrile, 2.56 g of a mixture of the title compound with its corresponding 6-carboxylic acid (73.5% yield); m.p. 249°-252° C. This was combined with 100 mg of the same product obtained previously by an analogous procedure.

Provenance & Evidence