Dimethylformamide → 4-(2-tert-butyl-1H-imidazol-5-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine

HRID 44915

Reaktionsgleichung

Reaktionsgleichung von HRID 44915
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:6]=12)=O.C[N:23]([CH:25]=O)C.[C:27]([O-])(=O)[C:28]([CH3:31])(C)[CH3:29].[Cs+].C([O-])(=O)C.[NH4+:39]>O>[C:28]([C:25]1[NH:23][C:3]([C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:6]=23)=[CH:2][N:39]=1)([CH3:31])([CH3:29])[CH3:27]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 517165Ammonium AcetateHCID 583616Cesium pivalateHCID 574775702-chloro-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)ethanone

Produkt 1

HCID 574775694-(2-tert-butyl-1H-imidazol-5-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridineAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)ethanone (prepared, e.g., as in Ex. 50, Step 1) (0.054 g, 0.00017 mol) in DMF (1.8 mL, 0.023 mol) was added cesium pivalate (0.0389 g, 0.000166 mol) and the reaction was stirred at room temperature for 16 hours. Ammonium acetate (0.45 g, 0.0058 mol) was added, and the reaction was heated in the microwave to 170° C. for 5 minutes. Water was added and the product was extracted with MTBE. The combined organic extracts were dried over sodium sulfate, then filtered and concentrated. The crude residue was purified by flash column chromatography (2.5% MeOH/DCM) to yield 4-(2-tert-butyl-1H-imidazol-5-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine (32 mg, 52%). 1H NMR (400 MHz, CDCl3): 8.31 (d, 1H), 7.50 (s, 1H), 7.40 (d, 1H), 7.37 (d, 1H), 6.94 (d, 1H), 5.69 (s, 2H), 3.52 (dd, 2H), 1.46 (s, 9H), 0.90 (dd, 2H), −0.08 (s, 9H); MS(ES): 371 (M+1).

Aufarbeitung

  1. temperaturethe reaction was heated in the microwave to 170° C. for 5 minutes
  2. extractionthe product was extracted with MTBE
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography (2.5% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-89b3030e1aee43b69129a8b520f25b85
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541425B2

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