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Potassium Carbonate → Ethyl 1-(3,4-difluorophenyl)-4[3-(ethoxycarbonyl)phenyl]-1H-pyrazole-3-carboxylate

HRID 587098
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 587098
Br[C:2]1[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[CH:8]=2)[CH:6]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=2)[C:31]([O:33][CH3:34])=[O:32])O1.[C:39](=O)([O-])[O-].[K+].[K+]>C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:9]1[CH:8]=[C:7]([N:5]2[CH:6]=[C:2]([C:36]3[CH:37]=[CH:28][CH:29]=[C:30]([C:31]([O:33][CH2:34][CH3:39])=[O:32])[CH:35]=3)[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:4]2)[CH:12]=[CH:11][C:10]=1[F:13]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27346513-Methoxycarbonylphenylboronic acid pinacol esterHCID 89464890ethyl 4-bromo-1-(3,4-difluorophenyl)-1H-pyrazole-3-carboxylate

Produkt 1

HCID 89464679Ethyl 1-(3,4-difluorophenyl)-4[3-(ethoxycarbonyl)phenyl]-1H-pyrazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 702EthanolLösungsmittel

Versuchsvorschrift

180 mg (0.54 mmol) of ethyl 4-bromo-1-(3,4-difluorophenyl)-1H-pyrazole-3-carboxylate, 156.7 mg (0.59 mmol) of methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, 158 mg (1.14 mmol) of potassium carbonate, 5.07 mg (0.011 mmol) of 2,2-dicyclohexylphosphino-2″,6″-diisopropoxybiphenyl and 1.22 mg (0.005 mmol) of palladium (II)acetate were suspended in 5 ml of ethanol and heated at the boil for 4 h. After cooling to room temperature, the solvent was removed under reduced pressure, the residue was dissolved in water and dichloromethane, the phases were separated and the organic phase was dried over magnesium sulfate. The crude product was purified by chromatography (ethyl acetate:n-heptane 1:4). This gave 84 mg (37%) of the desired product. 1H-NMR (400 MHz, CDCl3 δ, ppm) 8.15 (s, 1H); 8.05 (d, 1H); 7.96 (s, 1H); 7.74-7.69 (m, 2H); 7.53-7.47 (m, 2H); 7.28 (m, 1H); 4.48-4.34 (m, 4H); 1.43 (t, 3H); 1.29 (t, 3H)

Aufarbeitung

  1. temperatureheated at the boil for 4 h
  2. customthe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. customdichloromethane, the phases were separated
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. customThe crude product was purified by chromatography (ethyl acetate:n-heptane 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-d81fe33f664741ed9f685641a0ae0dee
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09226505B2

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