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

HRID 29005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29005
[I:1]Cl.[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[N:15]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[C:16]([Si](C)(C)C)=[CH:17][C:10]=23)[C:6]([C:31]2[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=2)=[N:5]1>C(#N)C>[I:1][C:16]1[N:15]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:11]2=[N:12][CH:13]=[CH:14][C:9]([C:7]3[C:6]([C:31]4[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=4)=[N:5][N:4]([CH3:3])[CH:8]=3)=[C:10]2[CH:17]=1

Komponenten

4

Edukt 2

HCID 24640Iodine chlorideHCID 689972904-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 689970402-iodo-4-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. concentrationThe reaction was concentrated to approx. ⅓ total volume
  2. additiondiluted with EtOAc (500 ml)
  3. washThe solution was washed with saturated NaHCO3(aq) (100 ml), saturated Na2S2O3(aq) (100 ml), brine (100 ml)
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration in vacuo
  6. customyielded a tan solid which
  7. customwas triturated with hot acetonitrile/Et2O

Quellen und Nachweise

ORD-Eintrag
ord-9e42a0feeb354792b99966e56e2c90d9
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419988B2

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