Potassium Phosphate, Tribasic → HCID 66899536, Verbindung
Reaktionsgleichung
[NH2:1][C:2]1[C:9](Br)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1Br.[CH:12]1(B(O)O)[CH2:14][CH2:13]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:39]2[CH2:44][CH2:43]CCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[C:9]([CH:12]2[CH2:14][CH2:13]2)=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH:43]1[CH2:44][CH2:39]1Komponenten
8
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Palladium (II) acetate (814 mg, 3.62 mmol) was added to a stirred mixture of 4-amino-3,5-dibromobenzonitrile (5.00 g, 18.1 mmol), cyclopropanboronic acid (3.89 g, 45.3 mmol), potassium phosphate tribasic (23.1 g, 109 mmol) and tricyclohexylphosphine (1.02 g, 3.62 mmol) in toluene (20.0 mL) and water (1.0 mL). The resulting mixture was degassed and heated to 100° C. After 3 h, the reaction mixture was cooled to rt, diluted with water and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (gradient elution, 0-15% EtOAc/hexanes as eluent) to afford the title compound i-7a. m/z (ES) 199 (MH)+.
Aufarbeitung
- customThe resulting mixture was degassed
- temperaturethe reaction mixture was cooled to rt
- additiondiluted with water
- extractionextracted with EtOAc
- washThe organics were washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude residue was purified by column chromatography on silica gel (gradient elution, 0-15% EtOAc/hexanes as eluent)
Quellen und Nachweise
- ORD-Eintrag
- ord-d4654b29fac44e449bb6c6ee0d85e9cb
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09029377B2
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