p-Anisoyl chloride → Ethyl 3-(4-methoxybenzamido)-1H-indole-2-carboxylate

HRID 1355627

Reaktionsgleichung

Reaktionsgleichung von HRID 1355627
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH2:15])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(N(CC)CC)C.[C:23](Cl)(=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 732887Ethyl 3-amino-1H-indole-2-carboxylate

Produkt 1

HCID 751363Ethyl 3-(4-methoxybenzamido)-1H-indole-2-carboxylateAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-2-indolecarboxylic acid ethyl ester (500 mg, 2.45 mmol) and triethylamine (272 mg, 2.70 mmol) in methylene chloride (5 mL) was added anisoyl chloride (418 mg, 2.45 mmol). The resulting mixture was stirred for 18 h at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was washed with 1 N aqueous hydrochloric acid, dried (sodium sulfate), filtered, and concentrated in vacuo to provide a yellow solid. Recrystallization from hexane/ethyl acetate provided 780 mg (94%) of the title compound as a yellow solid.

Aufarbeitung

  1. washwashed with water
  2. washThe organic phase was washed with 1 N aqueous hydrochloric acid
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a yellow solid
  7. customRecrystallization from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-209c1c53411c4a919ad228597f1cc357
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586459B2

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