반응 #2495266

반응 방정식

2-(3-bromo-phenyl)-6-fluoro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester

morpholine

N,N-dimethylglycine hydrochloride

potassium carbonate

→

6-fluoro-4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid

수율 61.4%

용매

dimethyl sulfoxide

반응 조건

후처리

1. 1
   추출The reaction mixture was extracted with ethyl acetate (150 mL×2)
2. 2
   세척washed with saturated aqueous ammonium chloride solution (50 mL×3) and brine (50 mL×2)
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   농축concentrated in vacuo
5. 5
   기타the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether)

실험 절차

A mixture solution of 2-(3-bromo-phenyl)-6-fluoro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (5 g, 12.7 mmol), morpholine (11.1 mL, 125 mmol), copper(I) iodide (1.43 g, 7.5 mmol), N,N-dimethylglycine hydrochloride (1.4 g, 10 mmol), and potassium carbonate (5.2 g, 75 mmol) in dimethyl sulfoxide (20 mL) was stirred at 120° C. for 16 h. Then the reaction mixture was cooled to room temperature. The reaction mixture was extracted with ethyl acetate (150 mL×2), washed with saturated aqueous ammonium chloride solution (50 mL×3) and brine (50 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether) to afford 6-fluoro-4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (3 g, 61%) as a white solid: MS (ESI) M+1=385.1.

출처