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Potassium Carbonate → N-(3,5-Bis-trifluoromethyl-benzyl)-6-(3-cyano-phenoxy)-N-methyl-4-o-tolyl-nicotinamide

HRID 1835369
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Reaktionsgleichung

Reaktionsgleichung von HRID 1835369
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](I)=[N:11][CH:10]=1.[OH:34][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[C:38]#[N:39].C(=O)([O-])[O-].[K+].[K+].COC(C)(C)C>N1C=CC=CC=1.[Cu-]=O>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([O:34][C:35]2[CH:42]=[CH:41][CH:40]=[C:37]([C:38]#[N:39])[CH:36]=2)=[N:11][CH:10]=1
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Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 15413tert-Butyl methyl etherHCID 10231844N-(3,5-Bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide

Produkt 1

HCID 23502813N-(3,5-Bis-trifluoromethyl-benzyl)-6-(3-cyano-phenoxy)-N-methyl-4-o-tolyl-nicotinamideAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419072HCID 178419072, VerbindungKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 200 mg (0.346 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide (Example 4) and 84 mg (0.69 mmol) 3-hydroxybenzonitrile in 4 ml pyridine was deoxygenated by three freeze-thaw cycles. After addition of 5 mg (0.04 mmol) copper(I) oxide and 96 mg (0.69 mmol) potassium carbonate under a stream of argon the reaction mixture was heated at reflux for 70 h. Cooling to room temperature was followed by dilution with tert-butyl methyl ether and washing with two portions of 1 M aqueous hydrochloric acid solution. The combined aqueous layers were extracted with tert-butyl methyl ether. The combined organic layers were washed with saturated aqueous sodium carbonate solution and brine, dried with sodium sulfate and concentrated. Column chromatography afforded 174 mg (88%) of the title compound as a light brown solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 70 h
  3. washwashing with two portions of 1 M aqueous hydrochloric acid solution
  4. extractionThe combined aqueous layers were extracted with tert-butyl methyl ether
  5. washThe combined organic layers were washed with saturated aqueous sodium carbonate solution and brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7ffcc908951e4c7f998cda365d29fe6c
Quelldatensatz
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06770637B2

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