تفاعل #1328419

معادلة التفاعل

5-hydroxy-1-methylpyrazole

potassium carbonate

triethylamine

5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole

carbon monoxide

carbon monoxide

→

(5-Hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazol-5-yl)methanone

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred for 24 hours
2. 2
   درجة الحرارةAfter cooling
3. 3
   أخرىthe solvent was removed
4. 4
   غسيلwashed with methylene chloride
5. 5
   استخلاصextracted with methylene chloride
6. 6
   غسيلThe combined organic phases were washed with saturated ammonium chloride solution
7. 7
   أخرىdried
8. 8
   أخرىthe solvent was removed

الإجراء التجريبي

0.62 g (6.33 mmol) of 5-hydroxy-1-methylpyrazole, 1.75 g (12.66 mmol) of dry potassium carbonate, 1.28 g (12.67 mmol) of triethylamine and 0.22 g (0.30 mmol) of bis-(triphenylphosphane)palladium dichloride were added to a suspension of 2.0 g (6.33 mmol) of 5-bromo-8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]-isoxazole in 100 ml of dioxane. In a miniautoclave, a carbon monoxide pressure of 20 bar was applied, the mixture was stirred for 5 minutes and the autoclave was vented. This procedure was repeated 3 times. The autoclave was subsequently heated to 1300° C., a carbon monoxide pressure of 20 bar was applied once more and the mixture was stirred for 24 hours. After cooling and venting, the solvent was removed, and the residue was taken up in water, adjusted to pH 11 and washed with methylene chloride. The mixture was subsequently acidified to pH 4 using 10 percent strength hydrochloric acid and extracted with methylene chloride. The combined organic phases were washed with saturated ammonium chloride solution and dried, and the solvent was removed. This gave 0.58 g (25%) of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)-(8-methylsulfonyl-3a,4-dihydro-3H-indeno[1,2-c]isoxazole)-methanone in the form of a dark oil.

المصدر