3-(Tributylstannyl)pyridine → 1-(3,5-Bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-imidazole-4-carbonitrile

HRID 349269

Reaktionsgleichung

Reaktionsgleichung von HRID 349269
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)[CH2:6][N:7]1[C:11](I)=[C:10]([C:13]#[N:14])[N:9]=[CH:8]1.C([Sn](CCCC)(CCCC)[C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)CCC>C(#N)C.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1)[CH2:6][N:7]1[C:11]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)=[C:10]([C:13]#[N:14])[N:9]=[CH:8]1

Komponenten

5

Edukt 2

HCID 34838483-(Tributylstannyl)pyridineHCID 866012221-(3,5-Bis-trifluoromethyl-benzyl)-5-iodo-1H-imidazole-4-carbonitrile

Produkt 1

HCID 866012211-(3,5-Bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-imidazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 498840Bis(benzonitrile)palladium chlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a pressure vessel dissolve 1-(3,5-Bis-trifluoromethyl-benzyl)-5-iodo-1H-imidazole-4-carbonitrile (0.52 g, 1.2 mmol) in acetonitrile. Add 3-tributylstannanyl-pyridine (0.64 g, 1.7 mmol) and bis(benzonitrile)dichloropalladium(II) (22 mg, 0.06 mmol), and stir at 100° C. After 72 h, quench with sat. aq. NaHCO3, and extract with ether. Wash the organic layer with brine, dry over MgSO4, filter, and concentrate. Purify by radial chromatography on silica gel to give the title compound: MS (ES) 397.2 (M+1); 1H NMR (300 MHz, CDCl3) δ 8.75 (d, J=4.6 Hz, 1H), 8.60 (ap d, 1H), 7.84 (s, 1H), 7.75 (s, 1H), 7.66 (m, 1H), 7.44 (m, 1H), 7.36 (s, 2H), 5.30 (s, 2H).

Aufarbeitung

  1. customquench with sat. aq. NaHCO3
  2. extractionextract with ether
  3. washWash the organic layer with brine
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by radial chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cc72bbe93a664215aa1a6308b75d81c9
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179804B2

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