تفاعل #71490

معادلة التفاعل

Sulfuryl chloride

5-(2-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester

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title compound

المردود 66.2%

5-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylicacid ethyl ester

المردود 66.2%

المذيبات

CH3CN

ظروف التفاعل

المعالجة

1. 1
   أخرىquenched by addition of a saturated solution of NaHCO3
2. 2
   تركيزconcentrated
3. 3
   workup.ADDITIONThe residue was diluted in EtOAc
4. 4
   أخرىThe aqueous phase was separated
5. 5
   استخلاصextracted with EtOAc
6. 6
   غسيلThe combined organic layers were washed with H2O and brine
7. 7
   تجفيفdried (Na2SO4)
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated
10. 10
    أخرىThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

الإجراء التجريبي

Sulfuryl chloride (75 μL, 0.93 mmol) was added dropwise to a cold (−20° C.) solution of 5-(2-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester (Step 176.3) (330 mg, 0.93 mmol) in CH3CN (6 mL). The reaction mixture was stirred for 10 min at −20° C., quenched by addition of a saturated solution of NaHCO3, and concentrated. The residue was diluted in EtOAc and a saturated solution of NaHCO3. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2) to provide 240 mg of the title compound as a white solid. Title compound: ESI-MS: 390.1 [M+H]+; tR=3.98 min (System 1); TLC: Rf=0.15 (Hex/EtOAc, 3:2).

المصدر