2-Fluoro-4-iodoaniline → 7-Fluoro-8-(2-fluoro-4-iodophenylamino)-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylic acid

Participants

Reaction Steps

8-Chloro-7-fluoro-6-oxo-2,3,4,6-tetrahydro-1H-quinolizine-9-carboxylic acid (7d, 426 mg, 1.74 mmol, 1 eq) and 2-fluoro-4-iodoaniline (827 mg, 3.49 mmol, 2 eq) were mixed in anhydrous THF (10 ml) at 0° C. under N2. 1N lithium hexamethyldisilazide in THF (5.23 ml, 5.23 mmol, 3 eq) was added drop wise and the mixture stirred for 4 hours while allowing the temperature to return to RT. The solution was evaporated and purified by flash chromatography using 10-16% MeOH in DCM as eluent. This afforded the title compound as a tan solid (216 mg, 28%). [M+H] calc'd for C16H13F2IN2O3, 447. found, 447.

Provenance & Evidence