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

HRID 349269

反応式

HRID 349269 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 498840Bis(benzonitrile)palladium chloride触媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cc72bbe93a664215aa1a6308b75d81c9
出典データセット
uspto-grants-2007_02
特許番号
US07179804B2

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