Ethyl chloroformate → HCID 86728308, compound

Participants

Reaction Steps

To a solution of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (100 mg, 0.163 mmol) in THF (2 mL) at −78° C. under N2 added n-butyllithium (0.203 ml, 0.325 mmol). After 10 mins, ethyl chloroformate (61.8 mg, 0.569 mmol) was added to the reaction mixture. And the reaction mixture was warmed to room temperature and stirred overnight under N2. The reaction mixture was quenched with 5 ml water extracted with 3×10 mL ethyl acetate. The organic layers were combined, washed with 2×5 mL of saturated brine, dried over anhydrous sodium sulfate and concentrated under vacuum. Silica gel chromatography eluted with ethyl acetate/hexane (20-100%) resulted in 38 mg (34%) of Ethyl (5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)benzofuran -3-carbonyl)(methyl)carbamate (Compound 208) as a white solid. LC-MS (ES, m/z) C35H28F2N4O7S: 686. Found: 687 [M+H]+.

Provenance & Evidence