Ethyl Acetoacetate → ethyl 4-(1-ethoxy-1,3-dioxobutan-2-yl)-7-o-tolyl-1H-indole-2-carboxylate

HRID 576269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576269
Cl[C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:6]2.[O:23]=[C:24]([CH3:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1C)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:29]([O:28][C:26](=[O:27])[CH:25]([C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:6]2)[C:24](=[O:23])[CH3:31])[CH3:30]

Komponenten

7

Edukt 4

HCID 8868Ethyl AcetoacetateHCID 62657Potassium Phosphate, TribasicHCID 27349372-(Di-tert-butylphosphino)-2'-methyl-1,1'-biphenylHCID 68936971ethyl 4-chloro-7-o-tolyl-1H-indole-2-carboxylate

Produkt 1

HCID 68940072ethyl 4-(1-ethoxy-1,3-dioxobutan-2-yl)-7-o-tolyl-1H-indole-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
93 °C

Versuchsvorschrift

A mixture of ethyl 4-chloro-7-o-tolyl-1H-indole-2-carboxylate (EXAMPLE 166C) (0.93 g), ethyl 3-oxobutanoate (0.849 g), di-tert-butyl(2′-methylbiphenyl-2-yl)phosphine (0.093 mg), K3PO4 (3.46 g), and palladium(II) acetate (0.033 g) in toluene (8 mL) was degassed via vacuum/nitrogen cycle three times. The reaction mixture was heated at 93° C. for 14 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified with flash chromatography on silica gel (ethyl acetate in hexanes) to give the title compound.

Aufarbeitung

  1. customwas degassed via vacuum/nitrogen cycle three times
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified with flash chromatography on silica gel (ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b54334d1a42d44c6934b3283461651bd
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09035047B2

Notizen zur Reaktion

Wird geladen…