تفاعل #57282

معادلة التفاعل

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

المردود 36.0%

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

المردود 36.0%

المذيبات

1,4-dioxane

NaHCO3

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   تركيزThe reaction was then concentrated
3. 3
   workup.ADDITIONdiluted with CHCl3 (200 ml) and EtOAc (200 ml)
4. 4
   أخرىsonicated for 10 minutes
5. 5
   ترشيحfiltered through Celite 545
6. 6
   تركيزconcentrated
7. 7
   أخرىto yield a red oil which
8. 8
   أخرىwas purified on 400 g silica gel (CHCl3/EtOAc w/0.1% MeOH)

الإجراء التجريبي

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.

المصدر