반응 #2495269

반응 방정식

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

1-o-tolyl-piperazine hydrochloride

xantphos

cesium carbonate

→

6-fluoro-4,4-dimethyl-2-[3-(4-o-tolyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester

수율 60.0%

용매

ethyl acetate

toluene

반응 조건

후처리

1. 1
   기타After colling to room temperature
2. 2
   세척washed with water (20 mL)
3. 3
   건조The organic layer was dried over anhydrous sodium sulfate
4. 4
   농축concentrated in vacuo
5. 5
   기타Purification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (50% ethyl acetate/hexanes)

실험 절차

A mixture of 2-(3-bromo-phenyl)-6-fluoro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (3.0 g, 7.65 mmol), 1-o-tolyl-piperazine hydrochloride (1.95 g, 9.2 mmol), palladium (II) acetate (172 mg, 0.77 mmol), xantphos (266 mg, 0.46 mmol) and cesium carbonate (5.0 g, 15.3 mmol) in toluene (20 mL) was heated for 3 h at 120° C. After colling to room temperature, the mixture was treated with ethyl acetate (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. Purification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (50% ethyl acetate/hexanes) to afford 6-fluoro-4,4-dimethyl-2-[3-(4-o-tolyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (2.2 g, 60%) as a white solid: MS (ESI) M+1=488.4.

출처