Pyridine → tert-butyl (1-(3,5-difluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate

HRID 1842937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842937
[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:21]=[C:22](B(O)O)[CH:23]=[C:24]([F:26])[CH:25]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:19][C:20]1[CH:21]=[C:22]([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:23]=[C:24]([F:26])[CH:25]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 59637276tert-butyl (3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate

Produkt 1

HCID 70855599tert-butyl (1-(3,5-difluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture tert-butyl (3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (251 mg, 0.946 mmol, 1 equiv.), 3,5-difluorophenylboronic acid (299 mg, 1.89 mmol, 2 equiv.) and copper acetate (258 mg, 1.49 mmol, 1.5 equiv.) in dichloromethane (14 mL) was added pyridine (151 mg, 0.151 mL, 1.89 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 dichloromethane (250 mL) and the solvent of the filtrate was evaporated to give tert-butyl (1-(3,5-difluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (214 mg, 60%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-63e9f1ba95954575bdc499636aecaff3
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946204B2

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