Potassium Phosphate, Tribasic → (S)-methyl 3-(sec-butylamino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-methyl 3-(sec-butylamino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (390 mg, crude) in dioxane (6 mL) was added 5-fluorobenzofuran-2-ylboronic acid (353 mg, 1.96 mmol), K3PO4 (416 mg, 1.96 mmol), Pd(PPh3)4 (64 mg, 0.06 mmol) and water (5 drops). The resulting solution was stirred for 1 h at 90° C. and then quenched by the addition of dichloromethane (100 mL). The resulting mixture washed with water (3×50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography eluting with 3.3% ethyl acetate in petroleum ether to afford (S)-methyl 3-(sec-butylamino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylate as a red solid (130.0 mg, 30% 2 steps).

Provenance & Evidence