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Potassium Carbonate → HCID 76283451, Verbindung

HRID 522312
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 522312
Br[CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[N:10][N:11]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:12]=2[CH3:13])[C:3]1=[O:21].[Cl:22][C:23]1[C:24]([C:29]([F:32])([F:31])[F:30])=[N:25][NH:26][C:27]=1[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:22][C:23]1[C:24]([C:29]([F:31])([F:30])[F:32])=[N:25][N:26]([CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]3[CH:9]=[N:10][N:11]([C:14]4[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=4)[C:12]=3[CH3:13])[C:3]2=[O:21])[C:27]=1[CH3:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12069654-Chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazoleHCID 86723025HCID 86723025, Verbindung

Produkt 1

HCID 76283451HCID 76283451, VerbindungAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-1-[1-(4-fluorophenyl)-5-methylpyrazol-4-yl]piperidin-2-one (0.05 g, 0.14 mmol) in DMF (1.0 mL) was added 4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazole (0.031 g, 0.17 mmol), followed by potassium carbonate (0.029 g, 0.21 mmol). After stirring at room temperature for 1 h, the reaction was quenched with water. The aqueous layer was then extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude product was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to give the title compound as a white solid (0.015 g, 0.025 mmol, 23%). 1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 7.44-7.35 (m, 2H), 7.22-7.13 (m, 2H), 4.94 (dd, J=9.9, 6.3 Hz, 1H), 3.90-3.70 (m, 2H), 2.73 (dddd, J=13.2, 11.5, 9.8, 3.3 Hz, I H), 2.47-2.38 (m, 1H), 2.36 (s, 3H), 2.31 (ddd, J=10.6, 5.4, 2.4 Hz, 1H), 2.17-2.12 (m, 1H), 2.13 (s, 3H); MS: (ES) m/z calculated for C20H18ClF4N5O [M+H]+ 456.1. found 456.1.

Aufarbeitung

  1. customthe reaction was quenched with water
  2. extractionThe aqueous layer was then extracted with ethyl acetate (2×25 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-3e2e3fc364834ceaa2852cb2b3c23c3e
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09328116B2

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