Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH2:10]([Si:12]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:13]#[C:14][CH2:15][CH2:16][OH:17])[CH3:11].[Cl-:22].[Li+].C(=O)([O-])[O-].[Na+].[Na+].C[N:31]([CH:33]=O)C>ClCCl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14]([CH2:15][CH2:16][OH:17])=[C:13]([Si:12]([CH2:20][CH3:21])([CH2:10][CH3:11])[CH2:18][CH3:19])[NH:8][C:5]2=[N:6][CH:7]=1.[Cl:22][C:3]1[CH:4]=[C:5]2[C:33](=[CH:7][C:2]=1[Cl:1])[NH:31][C:13]([Si:12]([CH2:10][CH3:11])([CH2:18][CH3:19])[CH2:20][CH3:21])=[C:14]2[CH2:15][CH2:16][OH:17]Komponenten
Edukt 5
Produkt 2
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol was prepared according to method D Step II with 5-chloro-3-iodopyridin-2-amine (2 g; 7.86 mmol), 4-(triethylsilyl)but-3-yn-1-ol (4.35 g; 23.58 mmol); (1,1′-bis(diphenylphosphino)ferrocene)-dichloromethane (0.321 g; 0.393 mmol), lithium chloride (0.333 g; 7.86 mmol) and sodium carbonate (1.67 g; 15.72 mmol) in DMF (15 mL) for approximately 20 hours. The crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 1.44 g (79%) of 2-(5,6-dichloro-2-(triethylsilyl)-1H-indol-3-yl)ethanol as a brown oil. The crude material was purified by flash chromatography on silica gel (eluent 7 to 80% of ethyl acetate in heptane) to give 2.15 g (88%) of 2-(5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol as a white solid.
Aufarbeitung
- customThe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)
Quellen und Nachweise
- ORD-Eintrag
- ord-4eacd43ffad54274a70e83131af6f831
- Quelldatensatz
- uspto-grants-2016_03
- Patentnummer
- US09284271B2
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