Water → [4-(4-chloro-benzyloxy)-3-fluoro-phenyl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

HRID 250623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250623
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Cl:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][C:18]=2[F:25])=[CH:13][CH:12]=1.[OH-].[K+].O>CO>[Cl:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][O:16][C:17]2[CH:24]=[CH:23][C:20]([CH:21]([C:3]3[C:4]4[C:9](=[N:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[OH:22])=[CH:19][C:18]=2[F:25])=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14797Potassium HydroxideHCID 580863304-((4-Chlorobenzyl)oxy)-3-fluorobenzaldehyde

Produkt 1

HCID 58086104[4-(4-chloro-benzyloxy)-3-fluoro-phenyl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 1H-Pyrrolo[2,3-b]pyridine (94, 100.0 mg, 0.85 mmol) in methanol (50.0 mL) were added 4-(4-chloro-benzyloxy)-3-fluoro-benzaldehyde (599, 250.0 mg, 0.94 mmol, prepared as described in Example 34) and potassium hydroxide (1.00 g, 17.82 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 30% ethyl acetate in hexane to give the compound (P-1895, 55 mg, 17.0%). MS (ESI) [M+H+]+=383.3.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-0b605ebba9d54a058f77bd2f62191504
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863288B2

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