Potassium Carbonate → 1h-Pyrazole-3-carboxamide,4-[3-(hydroxymethyl)phenyl]-1-[(4-methoxyphenyl)methyl]-n-phenyl-

HRID 132061

Reaktionsgleichung

Reaktionsgleichung von HRID 132061
[C:1]1([NH:7][C:8]([C:10]2[C:14](I)=[CH:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25](=[O:28])([O-])[O-].[K+].[K+]>C(O)C.C1(C)C=CC=CC=1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]1([NH:7][C:8]([C:10]2[C:14]([C:1]3[CH:6]=[CH:5][CH:4]=[C:3]([CH2:25][OH:28])[CH:2]=3)=[CH:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 668573141h-Pyrazole-3-carboxamide,4-iodo-1-[(4-methoxyphenyl)methyl]-n-phenyl-

Produkt 1

HCID 668554221h-Pyrazole-3-carboxamide,4-[3-(hydroxymethyl)phenyl]-1-[(4-methoxyphenyl)methyl]-n-phenyl-Ausbeute 263,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 86587398Ethanol toluene waterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 4-iodo-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide (50 mg; 0.11 mmol), bis(tri-tert-butylphosphine)palladium (12 mg), potassium carbonate (100 mg; 0.66 mmol) and 3-(hydroxmethyl)benzene boronic acid (21 mg; 0.14 mmol) in ethanol/toluene/water (4 ml:1 ml:1 ml) was heated at 120° C. (50 W) for 15 minutes in a CEM Discover microwave synthesiser. The reaction was evaporated and the residue partitioned between ethyl acetate and brine. The ethyl acetate layer was separated, dried (MgSO4), filtered and evaporated and the crude material purified by flash column chromatography eluting with 1:2 then 2:1 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 60 mg of 4-(3-hydroxymethyl-phenyl)-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide.

Aufarbeitung

  1. customThe reaction was evaporated
  2. customthe residue partitioned between ethyl acetate and brine
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude material purified by flash column chromatography
  8. washeluting with 1:2
  9. additionProduct containing fractions
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b08a7a61d5664d678345c07f72187e9e
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07385059B2

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