Реакция #535397

Уравнение реакции

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

Растворители

THF

Условия реакции

Обработка

1. 1
   Температураto cool to 23° C.
2. 2
   Другоеpartitioned between water (200 mL) and ethyl acetate (200 mL)
3. 3
   ПромывкаThe organic layer was washed with brine
4. 4
   Сушкаdried over sodium sulfate
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe residue was purified by flash column chromatography on silica gel
7. 7
   Промывкаeluting with hexane initially

Методика

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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