Réaction #45873

Équation de réaction

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

2-(tri-n-butylstannyl)thiophene

2,6-di-tert-butyl-p-cresol

→

compound

Rendement 96.0%

2-Cyclopropyl-7-fluoro-5-methyl-6-(thiophen-2-yl)-1,3-benzoxazole-4-carbonitrile

Rendement 96.0%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling to room temperature
2. 2
   Autrethe insoluble matter was separated by filtration
3. 3
   Lavagewith washing with ethyl acetate
4. 4
   LavageThe filtrate was washed with saturated brine
5. 5
   Séchagedried over anhydrous sodium sulfate
6. 6
   AutreThe insoluble matter was separated by filtration
7. 7
   Autrethe solvent was evaporated away
8. 8
   Autrethe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Mode opératoire

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-77) (200 mg, 0.68 mmol), 2-(tri-n-butylstannyl)thiophene (280 μl, 0.88 mmol) and 2,6-di-tert-butyl-p-cresol (2 grains) were dissolved in 1,4-dioxane (6 ml), and at room temperature, bis(triphenylphosphine)palladium(II) dichloride (48 mg, 0.07 mmol) was added. The solution was stirred under nitrogen atmosphere at 100° C. for 15 hours. After cooling to room temperature, the insoluble matter was separated by filtration with washing with ethyl acetate. The filtrate was washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=19:1, v/v) to obtain the entitled compound (194 mg, 96%) as a white solid.

Source