Reaktion #69149

Reaktionsgleichung

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

Ausbeute 87.5%

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

Ausbeute 87.5%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed
2. 2
   Sonstigedegassed 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
   Sonstigethe reaction mixture was degassed
6. 6
   workup.STIRRINGstirred under nitrogen for 2 hours
7. 7
   FiltrationThe resulting mixture was filtered
8. 8
   Waschenthe solid was washed with dioxane and water
9. 9
   SonstigeThe solid was dried in a vacuum oven

Vorschrift

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).

Quelle