Water → {5-[Hydroxy-(5-triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester

HRID 1256757Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1256757
[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[O:26])=[CH:21][N:20]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH:28]([Si:31]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[O:32][C:33]1[CH:34]=[C:35]2[CH:41]=[CH:40][NH:39][C:36]2=[N:37][CH:38]=1)([CH3:30])[CH3:29].[OH-].[K+].O>CO>[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([CH:25]([OH:26])[C:41]2[C:35]3[C:36](=[N:37][CH:38]=[C:33]([O:32][Si:31]([CH:42]([CH3:44])[CH3:43])([CH:45]([CH3:47])[CH3:46])[CH:28]([CH3:29])[CH3:30])[CH:34]=3)[NH:39][CH:40]=2)=[CH:21][N:20]=1)[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 59593275(5-Formyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl esterHCID 595933245-Triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 59593260{5-[Hydroxy-(5-triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl}-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl esterAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of (5-Formyl-pyridin-2-yl)-(4-trifluoromethyl-benzyl)-carbamic acid tert-butyl ester (19, 41 mg, 0.11 mmol, prepared as described in Example 30), 5-triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridine (83, 34 mg, 0.12 mmol) and potassium hydroxide (9.8 mg, 0.17 mmol) in methanol (10 mL) was stirred at room temperature overnight. The reaction mixture was poured into water, extracted with ethyl acetate, washed with brine and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a viscous liquid (84, 0.05 g, 70%). MS (ESI) [M+H+]+=671.38.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-a9c08b9af4b54262ab40f931a4ec300f
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461169B2

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