Hydrochloric Acid → {2,4-difluoro-3-[hydroxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenyl}-carbamic acid benzyl ester

HRID 250630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250630
Cl[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.CO.[OH-].[K+].[CH2:15]([O:22][C:23](=[O:35])[NH:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH:32]=[O:33])[C:26]=1[F:34])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>>[CH2:15]([O:22][C:23](=[O:35])[NH:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH:32]([OH:33])[C:10]2[C:4]3[C:5](=[N:6][CH:7]=[CH:2][CH:3]=3)[NH:8][CH:9]=2)[C:26]=1[F:34])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 58086235Benzyl (2,4-difluoro-3-formylphenyl)carbamate

Produkt 1

HCID 66679278{2,4-difluoro-3-[hydroxy-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenyl}-carbamic acid benzyl esterAusbeute 50,6 %

Versuchsvorschrift

Into a round bottom flask was added 5-chloro-1H-pyrrolo[2,3-b]pyridine (80, 0.524 g, 3.43 mmol, prepared as described in Example 9) in methanol (5.00 mL, 0.123 mol). Potassium hydroxide (0.800 g, 14.2 mmol) and (2,4-difluoro-3-formyl-phenyl)-carbamic acid benzyl ester (614, 1.02 g, 3.5 mmol) were added and the reaction mixture was stirred overnight. The reaction mixture was poured into 1N HCl and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and crystallized from ethyl acetate to give compound 615 (710 mg, 46%). MS (ESI) [M+H+]+=444.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customcrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1133bb74fdec4b0ab6f3c79394e7087a
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863288B2

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