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

HRID 349269

Reaction equation

HRID 349269 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-cc72bbe93a664215aa1a6308b75d81c9
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Linked notes

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