Potassium Phosphate, Tribasic → HCID 67315543, Verbindung

HRID 1011895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011895
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[N:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=2)[CH:9]=1)=[O:4].[O:18]1[C:22](B(O)O)=[CH:21][C:20]2[CH:26]=[CH:27][CH:28]=[CH:29][C:19]1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CC(O)=O.CC(O)=O.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:17])[N:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:22]2[O:18][C:19]3[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=3[CH:21]=2)[CH:9]=1)=[O:4]

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2776266Benzo[b]furan-2-boronic acidHCID 13370531HCID 13370531, Verbindung

Produkt 1

HCID 67315543HCID 67315543, VerbindungAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 4144353Palladium (II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1.40 g (4.74 mmol) of 5-(3-bromo-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (6′) (and ethyl ester) was dissolved in 15 ml of toluene and 1.6 ml of H2O. Then 1.54 g (9.49 mmol) of benzo[b]furan-2-boronic acid, 5.42 g (25.52 mmol) of K3PO4, 0.29 g (1.04 mmol) of tricyclohexylphosphine and 0.117 g (0.52 mmol) of palladium-II-acetate were added. The reaction mixture was degassed (argon) several times at each addition. The reaction was heated (100° C.) for 24 h. At RT, the mixture was partitioned between chilled water/EtOAc (3×). The organic phases were washed with water, with aqueous sat. NaHCO3, dried (Na2SO4), filtered (black palladium complex stayed with Na2SO4) and evaporated. Then the residual product was dissolved in hot CH2Cl2 and crystallized at RT. It was filtered to give 0.918 g (58%) of 5-(3-benzofuran-2-yl-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester as white powder. MS: 332.2 (M+).

Aufarbeitung

  1. customThe reaction mixture was degassed (argon) several times
  2. additionat each addition
  3. customAt RT, the mixture was partitioned
  4. temperaturebetween chilled water/EtOAc (3×)
  5. washThe organic phases were washed with water, with aqueous sat. NaHCO3
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered (black palladium complex stayed with Na2SO4)
  8. customevaporated
  9. dissolutionThen the residual product was dissolved in hot CH2Cl2
  10. customcrystallized at RT
  11. filtrationIt was filtered

Quellen und Nachweise

ORD-Eintrag
ord-3b03feb1f7244efd9c2ef1b08aa255d7
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977358B2

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