Potassium Carbonate → 4-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-carbaldehyde

HRID 1045186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1045186
Br[C:2]1[CH:3]=[N:4][N:5]([CH3:9])[C:6]=1[CH:7]=[O:8].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[N:4][N:5]([CH3:9])[C:6]=2[CH:7]=[O:8])=[CH:13][CH:12]=1

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 27946344-bromo-1-methyl-1H-pyrazole-5-carbaldehyde

Produkt 1

HCID 866425044-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

4-Bromo-1-methyl-1H-pyrazole-5-carbaldehyde (0.500 g), 4-chlorophenylboronic acid (0.455 g), tetrabutylammonium bromide (0.853 g), potassium carbonate (0.914 g) and palladium acetate (0.030 g) were stirred together in 5 mL of water and heated to 45° C. After stirring for 2.5 hours, the reaction was diluted with ethyl acetate (75 mL) and washed with water (25 mL), brine (50 mL), dried over magnesium sulfate, filtered and concentrated to give the crude material. The solid was chromatographed over silica gel (SF40-80) eluted using a gradient of 5% to 25% ethyl acetate/hexanes over 30 minutes.

Aufarbeitung

  1. washwashed with water (25 mL), brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-53acc79a5fbd47a4a2b88e5eb3f16c49
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563735B2

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