Citric Acid → 5-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxylic acid

HRID 733127

Reaktionsgleichung

Reaktionsgleichung von HRID 733127
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:10]([C:17]([O:19]CC)=[O:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:13]([C:12]1[N:8]([C:4]2[CH:3]=[C:2]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[Cl:22])[CH:7]=[CH:6][CH:5]=2)[N:9]=[C:10]([C:17]([OH:19])=[O:18])[CH:11]=1)([CH3:15])([CH3:16])[CH3:14]

Komponenten

10

Edukt 6

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 27343222-Chlorophenylboronic acidHCID 57428253ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylate

Produkt 1

HCID 112796905-tert-butyl-1-(2'-chloro-1,1'-biphenyl-3-yl)-1H-pyrazole-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylate and 2-chlorophenylboronic acid (0.279 g, 1.78 mmol) in n-propanol:water (2.35 ml:0.482 ml) mixture were added palladium acetate (0.005 g), triphenylphosphine (0.016 g) and 2N sodium carbonate (0.497 ml) and the solution was refluxed for 16 hours. To the reaction, a 2N solution of NaOH (1.5 ml) was added and refluxed for an additional 2 hours. The solution was cooled, acidified with 10% citric acid and extracted into ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 0.212 g of 5-tert-butyl-1-(2′-chloro-1,1′-biphenyl-3-yl)-1H-pyrazole-3-carboxylic acid.

Aufarbeitung

  1. temperaturethe solution was refluxed for 16 hours
  2. customTo the reaction
  3. temperaturerefluxed for an additional 2 hours
  4. temperatureThe solution was cooled
  5. extractionextracted into ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3b54fcb58b5f418dbddf2a237380cde7
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589116B2

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