تفاعل #57283

معادلة التفاعل

ICl

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

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title product

المردود 53.0%

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

المردود 53.0%

المذيبات

acetonitrile

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction was concentrated to approx. ⅓ total volume
2. 2
   workup.ADDITIONdiluted with EtOAc (500 ml)
3. 3
   غسيلThe solution was washed with saturated NaHCO3(aq) (100 ml), saturated Na2S2O3(aq) (100 ml), brine (100 ml)
4. 4
   تجفيفdried over MgSO4
5. 5
   ترشيحFiltration and concentration in vacuo
6. 6
   أخرىyielded a tan solid which
7. 7
   أخرىwas triturated with hot acetonitrile/Et2O

الإجراء التجريبي

To a solution of ICl (1M in CH2Cl2, 43.3 mmol) in acetonitrile (250 ml) at −10° C. was added a solution of 4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine (8.67 mmol) in acetonitrile (46 ml) followed by stirring at −10° C. for 5 minutes. The reaction was concentrated to approx. ⅓ total volume and then diluted with EtOAc (500 ml). The solution was washed with saturated NaHCO3(aq) (100 ml), saturated Na2S2O3(aq) (100 ml), brine (100 ml), and dried over MgSO4. Filtration and concentration in vacuo yielded a tan solid which was triturated with hot acetonitrile/Et2O, providing the title product as a light tan solid (53%). ESMS [M+H]+: 586.0.

المصدر