반응 #57282

반응 방정식

N2

4-bromo-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

1-methyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

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title product

수율 36.0%

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

수율 36.0%

용매

1,4-dioxane

NaHCO3

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   농축The reaction was then concentrated
3. 3
   workup.ADDITIONdiluted with CHCl3 (200 ml) and EtOAc (200 ml)
4. 4
   기타sonicated for 10 minutes
5. 5
   여과filtered through Celite 545
6. 6
   농축concentrated
7. 7
   기타to yield a red oil which
8. 8
   기타was purified on 400 g silica gel (CHCl3/EtOAc w/0.1% MeOH)

실험 절차

A mixture of 4-bromo-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine (37 mmol) and 1-methyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (37 mmol) in 1,4-dioxane (300 ml) and saturated NaHCO3(aq) (100 ml) was degassed with N2 for 10 minutes after which time tetrakis(triphenylphosphine) palladium(0) (1.85 mmol) was added and the resulting mixture was heated at 105° C. overnight. The reaction was then concentrated, diluted with CHCl3 (200 ml) and EtOAc (200 ml), sonicated for 10 minutes, filtered through Celite 545, and concentrated to yield a red oil which was purified on 400 g silica gel (CHCl3/EtOAc w/0.1% MeOH) to give the title product as a light yellow foam (36%). ESMS [M+H]+: 532.0.

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