Sodium Bicarbonate → HCID 86679808, Verbindung

HRID 1754563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754563
CC(C)([O-])C.[K+].[Cl:7][C:8]1[C:9]([F:16])=[CH:10][C:11]([I:15])=[C:12]([CH:14]=1)[NH2:13].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[N:23]1[CH:27]=[C:26]([C:28](F)=[O:29])[CH:25]=[N:24]1.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:7][C:8]1[C:9]([F:16])=[CH:10][C:11]([I:15])=[C:12]([NH:13][C:28]([C:26]2[CH:25]=[N:24][N:23]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)[CH:27]=2)=[O:29])[CH:14]=1

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 247872515-Chloro-4-fluoro-2-iodobenzenamineHCID 86039217HCID 86039217, Verbindung

Produkt 1

HCID 86679808HCID 86679808, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Potassium t-butoxide (12.52 g, 111.6 mmol) is added at room temperature to a solution of 5-chloro-4-fluoro-2-iodoaniline (5.0 g, 22.3 mmol) in 250 mL of anhydrous THF under nitrogen. After stirring for 15 minutes, a solution of 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylic acid fluoride (5.67 g, 24.6 mmol) in 30 mL of anhydrous THF is added dropwise. The reaction mixture is stirred for 4 hours at room temperature and then poured into saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic phase is washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated to dryness. After purification by flash chromatography on silica (cyclohexene/EtOAc: 95/5 to 80/20), a red solid is obtained, which is purified by flash chromatography on amine phase (DCM) to give 2.84 g of a white solid (yield: 31%).

Aufarbeitung

  1. stirringThe reaction mixture is stirred for 4 hours at room temperature
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with saturated aqueous NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customAfter purification by flash chromatography on silica (cyclohexene/EtOAc: 95/5 to 80/20)
  7. customa red solid is obtained
  8. customwhich is purified by flash chromatography on amine phase (DCM)

Quellen und Nachweise

ORD-Eintrag
ord-82f952c4b9d14ea888cf2bc662e58f7a
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169246B2

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