Benzothiazole → methyl 2-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-chloro-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate (300 mg, 0.98 mmol) in 1,3-benzothiazole (266 mg, 1.97 mmol) was added Pd(PPh3)4 (57 mg, 0.05 mmol,) and potassium acetate (193 mg, 1.97 mmol) under an atmosphere of nitrogen. The resulting solution was stirred for 2 h at 170° C. and then quenched by the addition of NH4Cl solution (150 mL), extracted with dichloromethane (3×20 mL) and the organic layers combined and dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography eluting with 1%-5% ethyl acetate in petroleum ether to afford methyl 2-(1,3-benzothiazol-2-yl)-3-[(2S)-2-methylpyrrolidin-1-yl]quinoxaline-6-carboxylate as a yellow solid (80 mg, 20%).

Provenance & Evidence