Methanol → (5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl)-(4-chloro-benzyl)-carbamic acid tert-butyl ester

HRID 1367289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367289
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CO.[C:13]([O:17][C:18](=[O:36])[N:19]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][N:21]=1)([CH3:16])([CH3:15])[CH3:14].[OH-].[K+]>O>[C:13]([O:17][C:18](=[O:36])[N:19]([C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:5]2[C:4]3[C:8](=[N:9][CH:10]=[C:2]([Br:1])[CH:3]=3)[NH:7][CH:6]=2)[OH:27])=[CH:22][N:21]=1)[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)([CH3:16])([CH3:14])[CH3:15]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 59593313(4-Chloro-benzyl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester

Produkt 1

HCID 59593354(5-[(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyridin-2-yl)-(4-chloro-benzyl)-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 5-bromo-7-azaindole (44, 198.0 mg, 1.01 mmol) in methanol (30.0 mL, 0.741 mol) were added (4-Chloro-benzyl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (43, 355.0 mg, 1.02 mmol) and potassium hydroxide (80.0 mg, 1.42 mmol). The reaction was stirred at room temperature 48 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography eluting with 8% methanol in dichloromethane to give compound (45, 200.0 mg, 36.8%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 8% methanol in dichloromethane
  7. customto give compound (45, 200.0 mg, 36.8%)

Quellen und Nachweise

ORD-Eintrag
ord-00c49e9502a347b89edd6b08a86270ca
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893075B2

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