反応 #535397

反応方程式

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

溶媒

THF

反応条件

後処理

1. 1
   温度to cool to 23° C.
2. 2
   その他partitioned between water (200 mL) and ethyl acetate (200 mL)
3. 3
   洗浄The organic layer was washed with brine
4. 4
   乾燥dried over sodium sulfate
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by flash column chromatography on silica gel
7. 7
   洗浄eluting with hexane initially

実験手順

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).

出典