반응 #57284

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2-iodo-4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

1,1-dimethylethyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyrimidinyl]-1-piperazinecarboxylate

NaHCO3

→

title compound

1,1-dimethylethyl 4-{5-[4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-pyrimidinyl}-1-piperazinecarboxylate

용매

1,4-dioxane

반응 조건

후처리

1. 1
   기타After degassing with argon for 10 minutes
2. 2
   온도Upon cooling
3. 3
   농축the reaction was concentrated
4. 4
   기타partitioned between EtOAc and H2O
5. 5
   세척The organic layer was washed with brine
6. 6
   건조dried (MgSO4)
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

To a solution of 2-iodo-4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.321 mmol) and 1,1-dimethylethyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyrimidinyl]-1-piperazinecarboxylate (0.353 mmol) in 1,4-dioxane (3 ml) was added saturated NaHCO3(aq) (0.85 ml). After degassing with argon for 10 minutes, dichlorobis(triphenylphosphine) palladium(II) (0.0161 mmol) was added and the resulting mixture was heated at 95° C. overnight. Upon cooling, the reaction was concentrated and partitioned between EtOAc and H2O. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated to yield the title compound as a yellow oil (quant.). ESMS [M+H]+: 722.2.

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