Réaction #57283

Équation de réaction

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

Rendement 53.0%

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

Rendement 53.0%

Solvants

acetonitrile

acetonitrile

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source