2-Fluoro-4-iodoaniline → 7-(2-Fluoro-4-iodo-phenylamino)-benzo[d]isothiazole-6-carboxylic acid tert-butyl ester

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Reaction Steps

To a solution of 7-fluoro-benzo[d]isothiazole-6-carboxylic acid tert-butyl ester (1.26 g, 5.0 mmol) and 2-fluoro-4-iodo-phenylamine (1.18 g, 5.0 mmol) in anhydrous THF (25 mL) at −78° C. was added a 1.0M solution of LHMDS in hexanes (10.0 mL, 10.0 mmol) under a nitrogen atmosphere. The reaction mixture was allowed to warm to room temperature and then stirred for 30 minutes before being quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated and washed with water followed by brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was subjected to flash chromatography (Si—PPC, gradient 0% to 10%, TBME in cyclohexane) to give the title compound as a yellow solid (717 mg, 30%). LCMS (method B): RT=5.14 min, [M+H]+=471.

Provenance & Evidence