反応 #57282

反応方程式

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

収率 36.0%

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

収率 36.0%

溶媒

1,4-dioxane

NaHCO3

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   濃縮The reaction was then concentrated
3. 3
   workup.ADDITIONdiluted with CHCl3 (200 ml) and EtOAc (200 ml)
4. 4
   その他sonicated for 10 minutes
5. 5
   ろ過filtered through Celite 545
6. 6
   濃縮concentrated
7. 7
   その他to yield a red oil which
8. 8
   その他was purified on 400 g silica gel (CHCl3/EtOAc w/0.1% MeOH)

実験手順

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.

出典