Ethyl4-(1-(3,4-Difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate → Ethyl2-tert-Butyl-3-(3,4-difluorobenzylcarbamoyl)-1H-indole-6-carboxylate

HRID 40114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40114
[CH2:1]([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:24](=O)[C:25]([CH3:28])([CH3:27])[CH3:26])[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=2)=[O:13])=[C:7]([N+:30]([O-])=O)[CH:6]=1)[CH3:2]>CO.[NH4+].[Cl-].[Zn]>[C:25]([C:24]1[NH:30][C:7]2[C:8]([C:11]=1[C:12](=[O:13])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1)=[CH:9][CH:10]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:33])[CH:6]=2)([CH3:28])([CH3:27])[CH3:26]

Komponenten

5

Edukt 1

HCID 59762433Ethyl4-(1-(3,4-Difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate2×

Produkt 1

HCID 59762341Ethyl2-tert-Butyl-3-(3,4-difluorobenzylcarbamoyl)-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

General Procedure R. To a solution of ethyl4-(1-(3,4-difluorobenzylamino)-4,4-dimethyl-1,3-dioxopentan-2-yl)-3-nitrobenzoate (Compound 114, 91 mg, 0.20 mmol) in MeOH (10 ml) and saturated aqueous NH4Cl (5 ml) was added zinc dust (320 mg, 4.9 mmol). The mixture was stirred at room temperature for 0.5 h, filtered and concentrated. The remaining aqueous suspension was extracted with EtOAc (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. extractionThe remaining aqueous suspension was extracted with EtOAc (×3)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e07e999b09bf429bae12abd21d92ba21
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524917B2

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