Triphenylphosphine → 3-[4-{3-Bromo-1-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)propyl}phenyl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine

HRID 573301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573301
[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([C:22]3[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25]4[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=4[N:23]=3)[CH2:19][CH2:20]O)=[CH:14][CH:13]=2)=[N:4]1)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:65])C(=O)C1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:65][CH2:20][CH2:19][CH:18]([C:15]1[CH:14]=[CH:13][C:12]([C:5]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:11]3[N:3]([CH2:1][CH3:2])[N:4]=2)=[CH:17][CH:16]=1)[C:22]1[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[C:25]2[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=2[N:23]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 866889713-[4-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl]-3-(1-[{2-(trimethylsilyl)ethoxy]methyl}-1H-benzo[d]imidazol-2-yl)propan-1-ol

Produkt 1

HCID 866889733-[4-{3-Bromo-1-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)propyl}phenyl]-1-ethyl-1H-pyrazolo[4,3-b]pyridineAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-{4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl}-3-(1-[(2-(trimethylsilyl)ethoxy)methyl]-1H-benzo[d]imidazol-2-yl)propan-1-ol (80 mg) and PPh3 (43.7 mg) in DMF (2 mL) was added NBS (27.0 mg) at room temperature. The mixture was stirred at room temperature under a dry atmosphere for 1 h. The mixture was neutralized with saturated NaHCO3 aqueous solution at 0° C. and extracted with AcOEt. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/AcOEt) to give the title compound (75 mg).

Aufarbeitung

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-4ccd111bbb8046ebbe19513a890ca7fd
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029536B2

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