4-Hydroxymethylpyridine → Ethyl 5-trifluoromethyl-1-[(pyrid-4-yl)methyl]-1H-indole-2-carboxylate

HRID 19743

Reaktionsgleichung

Reaktionsgleichung von HRID 19743
N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[F:19][C:20]([F:36])([F:35])[C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:24]2.[N:37]1[CH:42]=[CH:41][C:40]([CH2:43]O)=[CH:39][CH:38]=1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[F:36][C:20]([F:35])([F:19])[C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([CH2:43][C:40]1[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=1)[C:25]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:24]2

Komponenten

6

Edukt 4

HCID 114724-HydroxymethylpyridineHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 17389890Ethyl 5-(trifluoromethyl)-1H-indole-2-carboxylate

Produkt 1

HCID 68431838Ethyl 5-trifluoromethyl-1-[(pyrid-4-yl)methyl]-1H-indole-2-carboxylateAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of 1.47 g (5.83 mmol) of 1,1′-(azodicarbonyl)dipiperidine in 50 ml of toluene is added dropwise to a solution of 1 g (3.89 mmol) of ethyl 5-trifluoromethyl-1H-indole-2-carboxylate, 0.63 g (5.83 mmol) of 4-pyridylcarbinol and 1.46 ml (5.83 mmol) of tributylphosphine in 50 ml of toluene. The reaction mixture is stirred overnight at room temperature and then concentrated under reduced pressure and chromatographed on a column of silica (eluent: dichloromethane/methanol). 1.05 g of expected product are obtained.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customchromatographed on a column of silica (eluent: dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-e1512384160041ed81db09ff569b2607
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745467B2

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