Ethyl Acrylate → 5-(4-Fluorophenyl)-3-(1-methylethyl)-1-(2-pyrimidinyl)-1H-pyrazole 2-propenoic acid, ethyl ester

HRID 1032452Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1032452
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].Br[C:9]1[C:10]([CH:27]([CH3:29])[CH3:28])=[N:11][N:12]([C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1>CN(C=O)C.CCN(CC)CC.CCOCC.O.[Pd](Cl)Cl.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>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[N:11]=[C:10]([CH:27]([CH3:29])[CH3:28])[CH:9]=2)=[CH:15][CH:16]=1.[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3]

Komponenten

8

Edukt 2

HCID 8821Ethyl AcrylateHCID 148513232-[4-bromo-5-(4-fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]pyrimidine

Produkt 1

HCID 867442225-(4-Fluorophenyl)-3-(1-methylethyl)-1-(2-pyrimidinyl)-1H-pyrazole 2-propenoic acid, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Ethyl acrylate (16.2 ml, 0.15 mol) and bis-(triphenylphosphine) palladium (II) chloride (0.84 g, 0.0012 mol) in DMF (75 ml) and Et3N (75 ml) was heated together at reflux under N2 with stirring until a homogeneous solution resulted. 2-[4-Bromo-5-(4-fluorophenyl))-3-(1-methylethyl)-1H-pyrazol-1-yl]pyrimidine (3) (10.8 g, 0.03 mol) was added and the resulting solution was heated at reflux for 24 hours, during which, an additional 1 mol % of catalyst was added. The mixture was then cooled to room temperature and diluted with ether and water. The organic layer was separated and washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting solid (10.4 g) was recrystallized from hexane/ethyl acetate, mp 155°-162° C.

Aufarbeitung

  1. temperatureat reflux under N2
  2. customresulted
  3. temperaturethe resulting solution was heated
  4. temperatureat reflux for 24 hours, during which
  5. additionan additional 1 mol % of catalyst was added
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe resulting solid (10.4 g) was recrystallized from hexane/ethyl acetate, mp 155°-162° C.

Quellen und Nachweise

ORD-Eintrag
ord-599e09fcfe9f4ea09233983333bc5570
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04957971

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