Water → HCID 86692601, Verbindung

HRID 1748661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748661
CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:11][CH:10]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:28]1[N:33]=[CH:32][C:31]([NH:34][C:35]([C:37]2[CH:38]=[N:39][N:40]([C:43]3[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][N:44]=3)[C:41]=2[CH3:42])=[O:36])=[CH:30][C:29]=1[CH3:53]>O1CCOCC1.C(OCC)(=O)C>[CH3:42][C:41]1[N:40]([C:43]2[CH:48]=[CH:47][C:46]([C:49]([F:50])([F:52])[F:51])=[CH:45][N:44]=2)[N:39]=[CH:38][C:37]=1[C:35]([NH:34][C:31]1[CH:32]=[N:33][C:28]([C:9]2[CH2:14][CH2:13][CH:12]([C:15]([F:16])([F:17])[F:18])[CH2:11][CH:10]=2)=[C:29]([CH3:53])[CH:30]=1)=[O:36]

Komponenten

7

Edukt 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 115653404,4,5,5-Tetramethyl-2-[4-(trifluoromethyl)-1-cyclohexen-1-yl]-1,3,2-dioxaborolaneHCID 86692602HCID 86692602, Verbindung

Produkt 1

HCID 86692601HCID 86692601, VerbindungAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4,4,5,5-Tetramethyl-2-[4-(trifluoromethyl)cyclohex-1-en-1-yl]-[1,3,2] dioxaborolane (163 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (37 mg), sodium carbonate (144 mg) and water (1.0 ml) were added at room temperature to a solution of N-(6-bromo-5-methylpyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (200 mg) described in Reference Example 189 in 1,4-dioxane (3.0 ml), and stirred at 100° C. under radiation of microwave for an hour. After completion of the reaction, water and ethyl acetate were added, filtered through Celite and the filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) to give the titled compound (146 mg) as a white solid.

Aufarbeitung

  1. additionwere added
  2. filtrationfiltered through Celite
  3. extractionthe filtrate was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-e6832daeedfa484f92c6b5aca0a0122d
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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