Reaktionsgleichung
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][C:7]=23)[CH:3]=[N:2]1.CN(C=O)C.[H-].[Na+].Br[CH:31]([CH2:33][CH2:34][CH3:35])[CH3:32]>>[CH3:32][CH:31]([N:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][C:7]=23)[CH:3]=[N:2]1)[CH2:33][CH2:34][CH3:35]Komponenten
5
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
4-(1H-Pyrazol-4-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine (50 mg, 0.0002 mol) (see, Example 231, Step 1) was dissolved in DMF (2 mL, 0.02 mol) and cooled at 0° C. This solution was treated with sodium hydride (7.0 mg, 0.00029 mol) (60% in oil) and stirred for 15 min. The mixture was then treated with 2-bromopentane (40 mg, 0.0002 mol) and was stirred for 5 h. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give the crude product 4-[1-(1-methylbutyl)-1H-pyrazol-4-yl]-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine as an oil, LC/MS (M+H)+: 286.
Aufarbeitung
- stirringwas stirred for 5 h
- customThe reaction was partitioned between ethyl acetate and water
- washThe organic layer was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-e2ff01e8d120489aafb19d803486bf29
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08530485B2
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