반응 #67093

반응 방정식

6-bromo-1-(phenylsulfonyl)-1H-indazole-4-carbonitrile

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

potassium phosphate tribasic

→

title compound

수율 16.6%

6-(1H-Indol-4-yl)-1-(phenylsulfonyl)-1H-indazole-4-carbonitrile

수율 16.6%

용매

1,4-dioxane

water

반응 조건

후처리

1. 1
   온도cooled
2. 2
   기타evaporated in vacuo
3. 3
   기타The residue was partitioned between water (50 ml) and dichloromethane (100 ml)
4. 4
   기타The suspended solid was collected
5. 5
   기타the organics were separated by hydrophobic frit
6. 6
   농축concentrated to approx 50 ml
7. 7
   기타The precipitated solid was collected as a beige solid (1.93 g)
8. 8
   기타the filtrate purified by silica (300 g) cartridge

실험 절차

To a solution of 6-bromo-1-(phenylsulfonyl)-1H-indazole-4-carbonitrile (5 g, 13.80 mmol) in 1,4-dioxane (50 ml) and water (20 ml) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (4.03 g, 16.57 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (1.010 g, 1.380 mmol) and potassium phosphate tribasic (8.79 g, 41.4 mmol). The mixture was heated at 60° C. for 1 h, cooled and evaporated in vacuo. The residue was partitioned between water (50 ml) and dichloromethane (100 ml). The suspended solid was collected and the organics were separated by hydrophobic frit and concentrated to approx 50 ml. The precipitated solid was collected as a beige solid (1.93 g) and the filtrate purified by silica (300 g) cartridge using a gradient of ethyl acetate and cyclohexane, to give the title compound as a pale yellow solid (0.91 g). The solid collected during partitioning was purified by pre-absorbing onto florisil and purification by silica (100 g) cartridge on Flashmaster 11 using a gradient of dichloromethane and ethyl acetate to give a further quantity of the title compound as a pale yellow solid (0.45 g).

출처