Sodium Carbonate → methyl 3-(1-methylethyl)-7-nitro-1H-indole-5-carboxylate

HRID 852610

Reaktionsgleichung

Reaktionsgleichung von HRID 852610
Br[C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([N+:25]([O-:27])=[O:26])[C:12]=1[N:13]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])C(=O)C(F)(F)F)[C:5]([O:7][CH2:8]C)=[O:6].C(O[Na])=O.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][CH:22]([C:21]1[C:2]2[C:12](=[C:11]([N+:25]([O-:27])=[O:26])[CH:10]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)[NH:13][CH:20]=1)[CH3:23]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 86602879Ethyl 3-bromo-4-[(3-methyl-2-buten-1-yl)(trifluoroacetyl)amino]-5-nitrobenzoateHCID 178526064HCID 178526064, Verbindung

Produkt 1

HCID 69358662methyl 3-(1-methylethyl)-7-nitro-1H-indole-5-carboxylateAusbeute 135,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-bromo-4-[(3-methyl-2-buten-1-yl)(trifluoroacetyl)amino]-5-nitrobenzoate (D215) (12.9 g, 28.5 mmol, 1 equiv) in DMF (130 ml) were added HCOONa (1.94 g, 28.5 mmol, 1 equiv), Na2CO3 (7.54 g, 71.2 mmol, 2.5 equiv), Bu4NCI (8.7 g, 31.3 mmol, 1.1 equiv) and palladium (II) acetate (320 mg, 1.42 mmol, 0.05 equiv) and the resulting mixture was stirred under nitrogen for 1 h then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt and H2O and the two layers were separated. The insoluble material in the aqueous phase was filtered off through a pad of celite and the aqueous layer extracted twice with AcOEt. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo to give methyl 3-(1-methylethyl)-7-nitro-1H-indole-5-carboxylate (D218) (10.1 g, 128%) as a black solid which was used in the next step without further purification.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between AcOEt and H2O
  3. customthe two layers were separated
  4. filtrationThe insoluble material in the aqueous phase was filtered off through a pad of celite
  5. extractionthe aqueous layer extracted twice with AcOEt
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1296be22aad6463db62bdfedbffd8138
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253198B2

Verknüpfte Notizen

Wird geladen…