Trifluoroacetic acid → HCID 21249906, Verbindung

HRID 1956526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1956526
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH2:38][CH2:39][CH:40]=O)[CH:32]=1.FC(F)(F)C(O)=O.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[CH2:40][CH2:39][CH2:38][CH2:37][C:33]1[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 110190264-pyridin-3-ylbutanalHCID 21249905HCID 21249905, Verbindung

Produkt 1

HCID 21249906HCID 21249906, VerbindungAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of benzyl-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}amine (700 mg) and 4-pyridin-3-yl butyraldehyde (314 mg) were solvated in 30 mL dry methanol to which ca. 2 g powdered 3 Å molecular sieves were added. The pH of this mixture was adjusted to 5 by the addition of trifluoroacetic acid and then 441 mg sodium cyanoborohydride was added and the mixture atirred at room temperature. After 48 hours, the mixture was filtered through diatomaceous earth, concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:4:0; then 96:4:1) to give the title compound (676 mg).

Aufarbeitung

  1. additionwere added
  2. customatirred at room temperature
  3. filtrationthe mixture was filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel (methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-edb5be50bd0e4044bc142ae47ca5f612
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780437

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