반응 #493719

반응 방정식

5-bromo-6-methyl-3-nitro-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one

(2-fluoro-3-methylphenyl)boronic acid

potassium fluoride

→

title compound

5-(2-Fluoro-3-methylphenyl)-6-methyl-3-nitro-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one

용매

THF

반응 조건

후처리

1. 1
   온도to cool to 23° C.
2. 2
   기타partitioned between water (200 mL) and ethyl acetate (200 mL)
3. 3
   세척The organic layer was washed with brine
4. 4
   건조dried over sodium sulfate
5. 5
   농축concentrated
6. 6
   기타The residue was purified by flash column chromatography on silica gel
7. 7
   세척eluting with hexane initially

실험 절차

A deoxygenated mixture of 5-bromo-6-methyl-3-nitro-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one (2.00 g, 6.35 mmol), (2-fluoro-3-methylphenyl)boronic acid (1.95 g, 12.7 mmol), potassium fluoride (2.43 g, 41.9 mmol), and bis(tri-tert-butylphosphine) palladium(0) (0.333 g, 0.652 mmol) in THF (32 mL) was heated at 66° C. for 30 min. The reaction mixture was allowed to cool to 23° C., then partitioned between water (200 mL) and ethyl acetate (200 mL). The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel, eluting with hexane initially, grading to 50% EtOAc in hexanes to give the title compound. MS: m/z=345.1 (M+1).

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