HCID 10252039, Verbindung → 3-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acid

HRID 1739590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739590
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22]CC4C=CC=CC=4)=[O:21])[CH:18]=3)[NH:13][CH:12]=2)=[C:6]([O:30][CH3:31])[CH:5]=1>CN(C)C=O.C(O)=O.[Pd]>[CH3:31][O:30][C:6]1[CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:32])[CH:9]=[CH:8][C:7]=1[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:22])=[O:21])[CH:18]=2)[NH:13][CH:12]=1

Komponenten

5

Edukt 1

HCID 10252039HCID 10252039, Verbindung

Produkt 1

HCID 103372503-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 284Formic AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-[5-benzoxycarbonyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (3.46 grams, 8.06 mmol) in dimethylformamide (40 mL) and formic acid (2 mL) was added 10% palladium on carbon (1.5 grams). The resulting mixture was hydrogenated at 30 psi for 1.5 hours. The mixture was filtered through celite and the filtrate diluted with ethyl acetate. This solution was washed several times with 1 M hydrochloric acid (aq). The organics were then dried over magnesium sulfate and concentrated. Recrystallization from methylene chloride gave 3-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acid (1.97 grams, 73% yield).

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. additionthe filtrate diluted with ethyl acetate
  3. washThis solution was washed several times with 1 M hydrochloric acid (aq)
  4. dry with materialThe organics were then dried over magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization from methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-64322bc4749042dda6e38d1988468d9d
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965745

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