반응 #1518776

반응 방정식

boronic acid

2,4-dichloro-5,7-difluoro-3-methylquinoline

5-methylpyridine-3-boronic acid

sodium carbonate

→

4-chloro-5,7-difluoro-3-methyl-2-(5-methylpyridin-3-yl)quinoline

용매

water

1,4-dioxane

반응 조건

후처리

1. 1
   workup.WAITthe reaction was continued for 18 h
2. 2
   온도Upon completion, the reaction was cooled to rt
3. 3
   기타partitioned between EtOAc and water
4. 4
   세척The organic layer was washed with brine
5. 5
   건조dried over magnesium sulfate, and cond
6. 6
   기타The resulting crude product was purified by flash chromatography (silica gel, 0-30% EtOAc in hexanes)

실험 절차

A screw-cap vial was charged with 2,4-dichloro-5,7-difluoro-3-methylquinoline (600 mg, 2.42 mmol), 5-methylpyridine-3-boronic acid (348 mg, 2.54 mmol), dichlorobis(triphenylphosphine)palladium (II) (170 mg, 0.24 mmol), sodium carbonate (769 mg, 7.26 mmol), 1,4-dioxane (6.5 mL), and water (1.6 mL). The mixture was stirred at 95° C. for 22 h, then 0.2 additional equivalents of the aforementioned boronic acid were added and the reaction was continued for 18 h. Upon completion, the reaction was cooled to rt and partitioned between EtOAc and water. The organic layer was washed with brine, dried over magnesium sulfate, and cond. The resulting crude product was purified by flash chromatography (silica gel, 0-30% EtOAc in hexanes), affording 4-chloro-5,7-difluoro-3-methyl-2-(5-methylpyridin-3-yl)quinoline. Mass Spectrum (ESI) m/e=305.0 (M+1).

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