Pyridine → tert-butyl (1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate

HRID 1842875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842875
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:7]=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[NH:5][N:4]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:5]2[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[CH:7][C:3]([C:2]([F:1])([F:17])[F:18])=[N:4]2)=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 2856454-Fluorophenylboronic acidHCID 59637276tert-butyl (3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate

Produkt 1

HCID 70855842tert-butyl (1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of tert-butyl (3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (501 mg, 1.89 mmol, 1 equiv.), 4-fluorophenylboronic acid (529 mg, 3.78 mmol, 2 equiv.) and copper acetate (517 mg, 2.83 mmol, 1.5 equiv.) in dichloromethane (28 mL) was added pyridine (301 mg, 0.301 mL, 3.78 mmol, 2 equiv) and the mixture was stirred in the presence of air for 2 d at room temperature. The reaction mixture was filtered over silica gel, the filter cake was washed with 250 mL of dichloromethane and the solvent of the filtrate was evaporated to give tert-butyl (1-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (501 mg, 74%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over silica gel
  2. washthe filter cake was washed with 250 mL of dichloromethane
  3. customthe solvent of the filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-eebd84f8e3b24b54853ba1cb9444ead8
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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