Sodium Carbonate → Ethyl 5-(trifluoromethyl)-1-[6-(2-{[4'-(trifluoromethyl)biphenyl-4-yl]methoxy}phenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylate

HRID 1255163

Reaktionsgleichung

Reaktionsgleichung von HRID 1255163
Br[C:2]1[CH:35]=[CH:34][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:19]=[C:18]([N:20]3[C:24]([C:25]([F:28])([F:27])[F:26])=[C:23]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:22]=[N:21]3)[CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[F:36][C:37]([F:48])([F:47])[C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[F:26][C:25]([F:28])([F:27])[C:24]1[N:20]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][CH2:6][C:5]3[CH:34]=[CH:35][C:2]([C:41]4[CH:42]=[CH:43][C:38]([C:37]([F:48])([F:47])[F:36])=[CH:39][CH:40]=4)=[CH:3][CH:4]=3)[N:19]=2)[N:21]=[CH:22][C:23]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 67159752Ethyl 1-(6-{2-[(4-bromobenzyl)oxy]phenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 86633489Ethyl 5-(trifluoromethyl)-1-[6-(2-{[4'-(trifluoromethyl)biphenyl-4-yl]methoxy}phenyl)pyridin-2-yl]-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a flask containing the title compound from Example 2 Step A (40.0 mg, 0.073 mmol) were added 4-trifluoromethylphenyl boronic acid (21.0 mg, 0.110 mmol) and dichlorobis(triphenylphosphine)palladium(II) (2.6 mg, 0.004 mmol). Degassed acetonitrile (0.5 mL) and sodium carbonate (0.183 mL, 1.0 M aqueous, 0.183 mmol) were added, and the reaction mixture was stirred at 70° C. After 1.5 h, the reaction mixture was allowed to cool to ambient temperature, then was filtered through a short plug of silica gel, eluting with DCM. The Suzuki product was used in the subsequent step without further purification: LCMS m/z 612.2 [M+H]+.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. filtrationwas filtered through a short plug of silica gel
  3. washeluting with DCM
  4. customThe Suzuki product was used in the subsequent step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8bbe2e7937e446e4834ba674a6b1da48
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455638B2

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