Citric Acid → HCID 57951702, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 2-(4-(4-(tert-butylcarbamoyl)-2-nitrophenoxy)-2,5-difluorophenyl)acetate (A.6) To a solution of compound A.4 (500 mg, 2.66 mmol) and N-tert-butyl-4-chloro-3-nitrobenzamide (A.5) (682 mg, 2.66 mmol) in DMSO (25 ml), Cs2CO3 (1.73 g, 5.32 mmol) was added in one portion. The reaction mixture was stirred at 80° C. for 1 hour, diluted with ethyl acetate and then 10% citric acid was added to adjust pH=2. The aqueous layer was extracted with ethyl acetate (2×), the combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in methanol (10 ml) then chlorotrimethylsilane was added to the solution. The reaction was stirred at room temperature for 1 hour and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 30% ethyl acetate in hexane.eluent) to give compound A.6 (340 mg, 30%, 2 steps). LC-MS ESI (pos.) m/z: 423.1 (M+H).

Provenance & Evidence