Sodium Carbonate → 1H-Pyrrolo[2,3-B]pyridine-3-ethanol, 5-chloro-2-(triethylsilyl)-

HRID 1918641

Reaktionsgleichung

Reaktionsgleichung von HRID 1918641
[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-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=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

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-olHCID 110760102-Amino-5-chloro-3-iodopyridine

Produkt 1

HCID 110560231H-Pyrrolo[2,3-B]pyridine-3-ethanol, 5-chloro-2-(triethylsilyl)-Ausbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178478483HCID 178478483, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 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) was heated at 100° C. for approximately 20 hours. After cooling, the mixture was concentrated under reduced pressure and the residue was partitioned between brine and ethyl acetate. After separation the organic layer was evaporated and the residue 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

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between brine and ethyl acetate
  4. customAfter separation the organic layer
  5. customwas evaporated
  6. customthe residue was purified by flash chromatography on silica gel (eluent 7 to 80% of ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-4572b156eda04827b10f40a688a9287b
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618138B2

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