Ammonia → 6-benzyl-9-(3-bromo-4-fluorophenyl)-2,3,5,6,7,9-hexahydrothieno[3,2-b][1,7]naphthyridin-8(4H)-one 1,1-dioxide

Participants

Reaction Steps

A solution of N-benzylpiperidine-3,5-dione (Ziegler, J. Amer. Chem. Soc. (1973), 95, 7458-7464) (0.55 g, 2.5 mmol) in ethyl alcohol (5 ML) was treated with 2.0M ammonia in ethyl alcohol (1.25 mL, 2.5 mmol), stirred 4 hours in a sealed tube, treated with the product from Example 10C (0.33 g, 2.5 mmol), treated with 3-bromo-4-fluorobenzaldehyde (0.51 g, 2.5 mmol), stirred at 75° C. for 48 hours, cooled and concentrated. The residue was purified by flash chromatography over silica gel (5-10% ethanol/methylene chloride) to provide the title compound (0.28 g).]

Provenance & Evidence