Dichloromethane → 5-(9H-carbazol-4-yl)pyridine-2-carbonitrile

HRID 1877454

Reaktionsgleichung

Reaktionsgleichung von HRID 1877454
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][N:4]=1)#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl.FC(F)(F)S(O[C:33]1[C:45]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[NH:38][C:37]=2[CH:36]=[CH:35][CH:34]=1)(=O)=O>O1CCOCC1.O>[CH:36]1[C:37]2[NH:38][C:39]3[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:45]=2[C:33]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=2)=[CH:34][CH:35]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 583383234-Trifluoromethanesulphonyloxycarbazole

Produkt 1

HCID 583381745-(9H-carbazol-4-yl)pyridine-2-carbonitrileAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

0.72 g of 2-cyano-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridine, 3.3 g of caesium carbonate and 92 mg of 1,1′-bis(diphenyl-phosphino)ferrocenepalladium(II) dichloride as a complex with dichloromethane (1/1) [PdCl2(dppf).CH2Cl2] are successively added, under argon, to a solution of 0.8 g of 4-trifluoromethanesulphonyloxycarbazole, obtained in stage 1 of Example 1, in a mixture of 37 ml of dioxane and 12 ml of water. The reaction mixture is refluxed for 4 hours, cooled to ambient temperature, filtered through celite and concentrated under reduced pressure. The residue is subsequently purified by silica gel chromatography, elution being carried out with a mixture of cyclohexane and ethyl acetate (85/15 by volume), so as to give 0.24 g of 5-(9H-carbazol-4-yl)pyridine-2-carbonitrile in the form of a yellow solid, the characteristics of which are the following:

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. filtrationfiltered through celite and
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is subsequently purified by silica gel chromatography, elution
  5. additionbeing carried out with a mixture of cyclohexane and ethyl acetate (85/15 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-706ae1abb02f4764b4715e4440b369f7
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309721B2

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