Triphenylphosphine → 6-Bromo-5-(1-isopropyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid ethyl ester
Reaktionsgleichung
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[C:10]([Br:16])[CH:9]=2)=[O:5])[CH3:2].[CH:17]([N:20]1[CH2:25][CH2:24][CH:23](O)[CH2:22][CH2:21]1)([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH:23]1[CH2:24][CH2:25][N:20]([CH:17]([CH3:19])[CH3:18])[CH2:21][CH2:22]1)=[C:10]([Br:16])[CH:9]=2)=[O:5])[CH3:2]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a suspension of 5.7 g (20.0 mmol) 6-bromo-5-hydroxy-1H-indole-2-carboxylic acid ethyl ester in 120 mL tetrahydrofuran, 3.44 g (24.0 mmol) isopropyl-piperidin-4-ol and 6.30 g (24.0 mmol) triphenylphosphine were added. The suspension was cooled to 0° C. and 5.53 g (24.0 mmol) di-tert-butyl azodicarboxylate was added. The ice bath was removed and the reaction mixture was stirred for 18 h at room temperature. The volatile components were removed and the residue was chromatographed on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant to afford 6.2 g (76%) of the compound as a light-yellow foam.
Aufarbeitung
- additionwere added
- customThe ice bath was removed
- customThe volatile components were removed
- customthe residue was chromatographed on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant
Quellen und Nachweise
- ORD-Eintrag
- ord-4b5d9e30fc7b4282b9a64386311c57ff
- Quelldatensatz
- uspto-grants-2009_03
- Patentnummer
- US07507736B2
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