Sodium Carbonate → Ethyl 1-[6-(2-methoxy-5-methylphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 1255173

Reaktionsgleichung

Reaktionsgleichung von HRID 1255173
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Cl)[N:16]=2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])[CH3:2].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=1[C:17]1[N:16]=[C:15]([N:9]2[C:10]([C:11]([F:14])([F:13])[F:12])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]2)[CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 2773485(2-Methoxy-5-methylphenyl)boronic acidHCID 73012968Ethyl 1-(6-chloropyridin-2-yl)-5-(trifluoromethyl)-1h-pyrazole-4-carboxylate

Produkt 1

HCID 67159458Ethyl 1-[6-(2-methoxy-5-methylphenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a flask containing the title compound from Example 1 Step A (1.50 g, 4.69 mmol) were added 2-methoxy-5-methylphenyl boronic acid (0.779 g, 4.69 mmol) and trans-dichlorobis(triphenylphosphine) palladium (II) (329 mg, 0.469 mmol). Acetonitrile (12 mL) and sodium carbonate (11.7 mL, 1.0 M aqueous, 11.7 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70° C. for 18 h, then was allowed to cool to room temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 20% EtOAc in hexanes, then 20 to 100% EtOAc in hexanes) provided compound the title compound: LCMS m/z 406.4 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.12 (s, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.91 (t, J=8.0 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 7.19 (dd, J=8.0, 2.0 Hz, 1H), 6.91 (d, J=8.0 Hz, 1H), 4.39 (q, J=7.0 Hz, 2H), 3.87 (s, 3H), 2.35 (s, 3H), 1.40 (t, J=7.0 Hz, 3H).

Aufarbeitung

  1. customthe resulting mixture was degassed via nitrogen
  2. customsparge
  3. temperatureto cool to room temperature
  4. additionwas poured into water
  5. extractionThe mixture was extracted with EtOAc
  6. concentrationthe organic phase was concentrated in vacuo
  7. customPurification by chromatography on silica gel (0 to 20% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-a9f9bc5be0fa4d19a076922468c33e1e
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455638B2

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