Pyrazole → 3-(1-{[2-(1H-pyrazol-1-yl)-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

HRID 383781

Reaktionsgleichung

Reaktionsgleichung von HRID 383781
Br[C:2]1[CH:7]=[C:6]([C:8]([N:10]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1.[NH:35]1[CH:39]=[CH:38][CH:37]=[N:36]1.C(=NO)C1C(=CC=CC=1)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.[Cu-]=O>[N:35]1([C:2]2[CH:7]=[C:6]([C:8]([N:10]3[CH2:14][CH2:13][CH:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH2:11]3)=[O:9])[CH:5]=[CH:4][C:3]=2[C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[CH:39]=[CH:38][CH:37]=[N:36]1

Komponenten

7

Edukt 4

HCID 1048PyrazoleHCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 866577533-(1-{[2-Bromo-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

Produkt 1

HCID 468475913-(1-{[2-(1H-pyrazol-1-yl)-3',5'-bis(trifluoromethyl)biphenyl-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419072HCID 178419072, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 3b (54.0 mg, 0.099 mmol), pyrazole (50.7 mg, 0.745 mmol), salicylaldoxime (19.8 mg, 0.145 mmol), copper(I) oxide (16.6 mg, 0.116 mmol) and cesium carbonate (265 mg, 0.812 mmol) in acetonitrile (1.00 mL) was heated to 120° C. in a sealed microwave vial for a total of 60 min. The reaction mixture was cooled to rt, concentrated in vacuo, and the resulting crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 10a. m/z (ES) 531 (MH)+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customthe resulting crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)

Quellen und Nachweise

ORD-Eintrag
ord-a453bc123ad646129051bb5ef7295e14
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367679B2

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