تفاعل #493719

معادلة التفاعل

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto cool to 23° C.
2. 2
   أخرىpartitioned between water (200 mL) and ethyl acetate (200 mL)
3. 3
   غسيلThe organic layer was washed with brine
4. 4
   تجفيفdried over sodium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by flash column chromatography on silica gel
7. 7
   غسيلeluting with hexane initially

الإجراء التجريبي

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).

المصدر