Toluene → HCID 68313548, compound

Participants

Reaction Steps

A mixture of Example 54A (419 mg, 1.45 mmol), toluene (0.2 mL), and sodium fluoride (21.3 mg, 0.507 mmol) was heated in a 120° C. oil bath and trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (1.43 mL, 7.24 mmol) was added via syringe pump over 2 hours. After 2 hours, the mixture was diluted with EtOAc (50 mL) and washed with saturated aqueous NaHCO3 (25 mL) and brine (10 mL), dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (0-25% EtOAc/hexanes, gradient elution) to provide the title compound (145 mg, 0.427 mmol, 30% yield). MS (DCI) M/Z 357 [M+NH4]+.

Provenance & Evidence