Water → (S)-methyl 2-(1H-indazol-5-yl)-3-(methyl(1-phenylethyl)amino)quinoxaline-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-methyl 3-(methyl(1-phenylethyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (432 mg, crude) in ethylene glycol dimethyl ether (5 mL) was added tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (201 mg, 0.58 mmol), K2CO3 (55 mg, 0.40 mmol), Pd(PPh3)4 (392 mg, 0.34 mmol) and water (1.5 mL) with stirring overnight at 90° C. in an oil bath. The resulting mixture was concentrated under vacuum, dissolved in water (100 mL), extracted with ethyl acetate (3×30 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified via silica gel chromatography (10% ethyl acetate in petroleum ether) to afford (S)-methyl 2-(1H-indazol-5-yl)-3-(methyl(1-phenylethyl)amino)quinoxaline-6-carboxylate as a yellow solid (144 mg).

Provenance & Evidence