N, N-dimethyl-(1-iodoethoxy)carbonyloxyacetamide → {1-[(1-Carbamoyl-6-chloro-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidene)-thiophen-2-ylmethoxy]-ethoxycarbonyloxy}-N,N-dimethylacetamide

Participants

Reaction Steps

The tetrabutylammonium salt of 3-[hydroxy-(2-thienyl)methylene]-6-chloro-5-fluoro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide (6.25 g) and N, N-dimethyl-(1-iodoethoxy)carbonyloxyacetamide (5.55 g) were combined in 60 mL of acetone, and the solution stirred for 90 hr. at 20° C. The precipitate present was removed by filtration and dried in vacuo. The solids were chromatographed on silica gel, eluting with 90:10 chloroform:acetone. Fractions containing the title product were combined and evaporated. The residue was slurried with a small amount of ethyl ether and filtered to give 820 mg of yellow solid, mp 194.5°-195.5° C.

Provenance & Evidence