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

HRID 29004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29004
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:3]=12.[CH3:24][N:25]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[C:27]([C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=2)=[N:26]1.N#N>O1CCOCC1.C([O-])(O)=O.[Na+].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:24][N:25]1[CH:29]=[C:28]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([S:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)(=[O:17])=[O:16])[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:3]=23)[C:27]([C:39]2[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=2)=[N:26]1

Komponenten

7

Edukt 3

HCID 947NitrogenHCID 687417291-methyl-3-(4-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 689992204-bromo-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 689972904-[1-methyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1-(phenylsulfonyl)-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwas added
  2. concentrationThe reaction was then concentrated
  3. additiondiluted with CHCl3 (200 ml) and EtOAc (200 ml)
  4. customsonicated for 10 minutes
  5. filtrationfiltered through Celite 545
  6. concentrationconcentrated
  7. customto yield a red oil which
  8. customwas purified on 400 g silica gel (CHCl3/EtOAc w/0.1% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-016b2a4a8c074d0094cf670ee8542b67
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419988B2

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