Pyridine → 2-Amino-5-[1-(4-cyanophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]-6-(2-furyl)nicotinonitrile

HRID 353231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 353231
[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:7]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[NH:17][CH:16]=2)=[CH:6][C:3]=1[C:4]#[N:5].[C:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)#[N:23].N1C=CC=CC=1.CN(C)C=O>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[NH2:1][C:2]1[N:9]=[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:7]([C:15]2[CH:20]=[CH:19][C:18](=[O:21])[N:17]([C:27]3[CH:28]=[CH:29][C:24]([C:22]#[N:23])=[CH:25][CH:26]=3)[CH:16]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 27343264-Cyanophenylboronic acidHCID 99654582-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile

Produkt 1

HCID 129921402-Amino-5-[1-(4-cyanophenyl)-6-oxo-1,6-dihydro-3-pyridinyl]-6-(2-furyl)nicotinonitrileAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 165397Cupric acetate monohydrateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

2-Amino-6-(2-furyl)-5-(6-oxo-1,6-dihydro-3-pyridinyl)nicotinonitrile (20 mg, 0.071 mmol), 4-cyanophenylboronic acid (35 mg, 0.24 mmol), copper acetate monohydrate (3.0 mg, 0.015 mmol), pyridine (0.015 mL, 0.19 mmol) and N,N-dimethylformamide (1.0 mL) were introduced into a reaction vessel and stirred at room temperature for 20 hours. Water was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was dried, and then dissolved in dimethyl sulfoxide (1.0 mL) and purified by high performance liquid chromatography, to give the title compound as a yellow solid (8.32 mg, 62%).

Aufarbeitung

  1. extractionby extracting with ethyl acetate
  2. customThe organic layer was dried
  3. dissolutiondissolved in dimethyl sulfoxide (1.0 mL)
  4. custompurified by high performance liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7c747ebadead41eba90261d209f3ff9d
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06750232B2

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