Cesium carbonate → 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate

HRID 1877467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1877467
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([F:15])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[CH:64]1[C:76]2[NH:75][C:74]3[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=3)[C:68]=2[C:67]([C:77]2[CH:78]=[CH:79][C:80]([C:83]#[N:84])=[N:81][CH:82]=2)=[CH:66][CH:65]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:83]([C:80]1[N:81]=[CH:82][C:77]([C:67]2[C:68]3[C:69]4[C:74](=[CH:73][CH:72]=[CH:71][CH:70]=4)[N:75]([C:2]4[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([F:15])[CH:3]=4)[C:76]=3[CH:64]=[CH:65][CH:66]=2)=[CH:78][CH:79]=1)#[N:84]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 46738774tert-Butyl 4-bromo-2-fluorobenzoateHCID 583381745-(9H-carbazol-4-yl)pyridine-2-carbonitrile

Produkt 1

HCID 583382932-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

0.63 g of 2-methylpropan-2-yl 4-bromo-2-fluorobenzoate, 1.88 g of caesium carbonate, 0.11 g of (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) and 0.03 g of palladium acetate are successively added, under argon, to a solution of 0.41 g of 5-(9H-carbazol-4-yl)pyridine-2-carbonitrile, obtained in stage 1 of Example 28, in 20 ml of dioxane. The reaction mixture is refluxed for 4 and a half hours, cooled to ambient temperature, filtered through celite and concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (90/10 by volume), so as to give 0.48 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-fluorobenzoate in the form of a light brown oil, the characteristics of which are the following:

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 4 and a half hours
  2. filtrationfiltered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by silica gel chromatography, elution
  5. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (90/10 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-6fd36c40bdcb408d896d481550e87c05
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309721B2

Notizen zur Reaktion

Wird geladen…