3-Fluorobenzenesulfonyl Chloride → HCID 67440485, compound

Participants

Reaction Steps

To an ice-cold mixture of 2-(3-amino-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (0.19 mmol, 1.0 eq.) in pyridine (5 mL) was added 3-fluorobenzene-1-sulfonyl chloride (0.29 mmol, 1.5 eq.) under nitrogen. Then the reaction mixture was stirred at room temperature for two hours. Thin layer chromatography and LC-MS indicated that the starting material was consumed completely. The reaction was quenched with 20 mL water extracted with ethyl acetate (20 mL×2). The combined organic layers were concentrated and the residue was purified by column chromatography (petroleum ether/ethyl acetate=1:1) to afford 2-(4-fluoro-3-(3-fluorophenylsulfonamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a pale yellow solid; Yield: 65%; MS (ESI+APCI) M+1=473.

Provenance & Evidence