Potassium Phosphate, Tribasic → HCID 67314101, Verbindung

HRID 1011864

Reaktionsgleichung

Reaktionsgleichung von HRID 1011864
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:19][CH3:20])=[N:7][N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](Br)[CH:13]=2)[C:9]=1[CH2:10][CH3:11])=[O:4].[Cl:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/B(O)O)=[CH:24][CH:23]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[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>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:19][CH3:20])=[N:7][N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](/[CH:29]=[CH:28]/[C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)[CH:13]=2)[C:9]=1[CH2:10][CH3:11])=[O:4]

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 642694trans-2-(4-Chlorophenyl)vinylboronic acidHCID 67313992HCID 67313992, Verbindung

Produkt 1

HCID 67314101HCID 67314101, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2.10 g (5.0 mmol) of 1-(3-bromo-phenyl)-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester and 1.82 g (10.0 mmol) of (E)-2-(4-chlorophenyl)vinyl boronic acid were dissolved in 50 ml of DMF. 12.5 ml of anhydrous potassium phosphate (tribasic, 2 M in water) were added drop by drop below 25° C., followed by 0.29 g (0.2 mmol) of tetrakis-(triphenylphosphine)-palladium. The reaction mixture was then stirred at 80° C. for 20 hours, cooled to RT, poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (n-heptane:EtOAc 1:0-8:2) to afford the title compound as light yellow solid. MS: 395.0 (MH+, 1 Cl).

Aufarbeitung

  1. temperaturecooled to RT
  2. additionpoured
  3. extractionextracted twice with CH2Cl2
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (n-heptane:EtOAc 1:0-8:2)

Quellen und Nachweise

ORD-Eintrag
ord-e931c22080bb4566aac8b189cc661612
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977358B2

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