반응 #90742

반응 방정식

(R)-3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

K2CO3

water

→

(R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

수율 87.4%

용매

dioxane H2O

반응 조건

후처리

1. 1
   추출extracted with DCM
2. 2
   세척The combined organic layer was washed with water, brine
3. 3
   건조dried over anhydrous Na2SO4
4. 4
   농축Concentrated in vacuo
5. 5
   기타the residue was purified with silica gel chromatography with PE/EA=1/1

실험 절차

The mixture of (R)-3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (80 mg, 0.125 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (59 mg, 0.150 mmol), Pd(PPh3)2Cl2 (9.2 mg, 0.0125 mmol) and K2CO3 (43 mg, 0.313 mmol) in dioxane/H2O (3 mL/0.3 mL) was stirred for 2 h at 90° C. under nitrogen atmosphere. Then the mixture was added water and extracted with DCM. The combined organic layer was washed with water, brine and dried over anhydrous Na2SO4. Concentrated in vacuo and the residue was purified with silica gel chromatography with PE/EA=1/1 to give (R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (90 mg, yield 87.2%) as yellow solid.

출처