반응 #69149

반응 방정식

potassium carbonate

5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

4-chloro-2-(methylthio)pyrimidine-5-carbonitrile

→

title compound

수율 87.5%

4-(5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile

수율 87.5%

용매

dioxane

반응 조건

후처리

1. 1
   기타was degassed
2. 2
   기타degassed again
3. 3
   workup.STIRRINGThe reaction mixture and stirred under nitrogen for 10 minutes
4. 4
   workup.ADDITIONWater (1.35 mL) was added
5. 5
   기타the reaction mixture was degassed
6. 6
   workup.STIRRINGstirred under nitrogen for 2 hours
7. 7
   여과The resulting mixture was filtered
8. 8
   세척the solid was washed with dioxane and water
9. 9
   기타The solid was dried in a vacuum oven

실험 절차

A mixture of 5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (306 mg, 0.74 mmol) and 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (207 mg, 1.12 mmol) in dioxane (9 mL) was degassed and stirred under nitrogen for 10 minutes. The reaction mixture was treated with potassium carbonate (336 mg, 2.23 mmol) and bis(tri-t-butylphosphine)palladium(0) (38 mg, 0.074 mmol) and degassed again. The reaction mixture and stirred under nitrogen for 10 minutes. Water (1.35 mL) was added and the reaction mixture was degassed and stirred under nitrogen for 2 hours. A suspension was observed. The resulting mixture was filtered and the solid was washed with dioxane and water. The solid was dried in a vacuum oven to afford the title compound as a white solid (282 mg, 87% yield).

출처