Sodium Carbonate → 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-chlorobiphenyl-2-yl) amide

HRID 346814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346814
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][N:14]([CH3:16])[CH:15]=1)=[O:10].[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9]([C:11]2[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][N:14]([CH3:16])[CH:15]=2)=[O:10])=[CH:24][CH:23]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 179479961-Methyl-3-trifluoromethyl-1h-pyrazole-4-carboxylic acid(2-bromo-phenyl)amide

Produkt 1

HCID 587994761-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-chlorobiphenyl-2-yl) amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid(2-bromo-phenyl)amide (0.64 g), 4-chlorobenzene boronic acid (0.29 g), powdered sodium carbonate (0.25 g) and tetrakis(triphenylphosphine) palladium (0.04 g) in 25 ml 1,2-dimethoxyethane (DME) and 2 ml water is heated at reflux temperature for 20 hours. After cooling, the solvent is removed in a water jet vacuum and the residue taken up in ethylacetate/water. The ethylacetate phase is washed twice with water and brine and then dried over sodium sulfate. Distilling off the solvent left the raw material which can be further purified by column chromatography (silicagel; eluant: ethylacetate/hexane 1:1) or recrystallization from TBME/hexane. The yield after purification is 0.6 g; m.p.=145–146° C.

Aufarbeitung

  1. temperatureat reflux temperature for 20 hours
  2. temperatureAfter cooling
  3. customthe solvent is removed in a water jet vacuum
  4. washThe ethylacetate phase is washed twice with water and brine
  5. dry with materialdried over sodium sulfate
  6. distillationDistilling off the solvent
  7. waitleft the raw material which
  8. customcan be further purified by column chromatography (silicagel; eluant: ethylacetate/hexane 1:1) or recrystallization from TBME/hexane
  9. customThe yield
  10. customafter purification

Quellen und Nachweise

ORD-Eintrag
ord-6c221704ba22411d94f61e1a06afe252
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173055B1

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