Reacción #45545

Ecuación de reacción

hydrochloric acid

7-bromo-2-tert-butyl-6-iodo-5-methyl-1,3-benzoxazole-4-carbonitrile

2-phenyl-1,3,2-dioxaborinane

potassium phosphate

→

compound

Rendimiento 44.0%

7-Bromo-2-tert-butyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Rendimiento 44.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Extracciónthe product was extracted with ethyl acetate (100 ml×2)
3. 3
   Lavadothe organic layer was washed with saturated brine (50 ml×2)
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1→6:1)

Procedimiento

Tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.26 mmol) was added to an N,N-dimethylformamide (60 ml) suspension of 7-bromo-2-tert-butyl-6-iodo-5-methyl-1,3-benzoxazole-4-carbonitrile (I-8) (545 mg, 1.30 mmol), 2-phenyl-1,3,2-dioxaborinane (205 μl, 1.37 mmol), anhydrous potassium phosphate (552 mg, 2.60 mmol), followed by stirring at 100° C. for 1 hour. After cooling, 1 N hydrochloric acid (100 ml) was added, the product was extracted with ethyl acetate (100 ml×2), the organic layer was washed with saturated brine (50 ml×2), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1→6:1) to obtain the entitled compound (210 mg, 44%) as a colorless solid.

Fuente