Stannane, tributyl(1-ethoxyethenyl)- → HCID 22380334, compound

HRID 1988704Notes

Reaction equation

HRID 1988704 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10](Br)=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:13][C:14]1[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[N:16]=[CH:17][CH:18]=1)[CH3:2].C([Sn](CCCC)(CCCC)[C:31]([O:33]CC)=[CH2:32])CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:31](=[O:33])[CH3:32])=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:13][C:14]1[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[N:16]=[CH:17][CH:18]=1)[CH3:2]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 22379886HCID 22379886, compound

Product 1

HCID 22380334HCID 22380334, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-Ethyl-2-{[2-(3-fluorophenyl)-pyrazol-3-yl]methyl}-5-bromo-1H-benzimidazole (200 mg, 0.5 mmol), tributyl(1-ethoxyvinyl)tin (0.34 ml, 1.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (29 mg) in toluene (10 mL) is heated at reflux for 1 h under argon. The solvent is removed in vacuo, the residue is then dissolved in 10% HCl (5 mL) and THF (5 mL). The mixture is stirred at room temperature for 0.5 h, then extracted with ethyl acetate. The aqueous layer is adjusted to pH 9, extracted with dichloromethane, and the organic layer dried (Na2SO4), concentrated, and the residue purified by preparative silica gel chromatography to give 1-Ethyl-2-{[2-(3-fluorophenyl)-pyrazol-3-yl]methyl}-5-acetyl-1H-benzimidazole. 1H NMR (CDCl3): δ 8.36 (d, 1H); 7.99 (dd, 1H); 7.645 (d, 1H); 7.25-7.49 (m, 4H); 7.14 (m, 1H); 6.21 (d, 1 h); 4.36 (s, 2H); 4.02 (g, 2H); 2.68 (s, 3H); 1.24 (t, 3H).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 h under argon
  3. customThe solvent is removed in vacuo
  4. dissolutionthe residue is then dissolved in 10% HCl (5 mL)
  5. extractionextracted with ethyl acetate
  6. extractionextracted with dichloromethane
  7. dry with materialthe organic layer dried (Na2SO4)
  8. concentrationconcentrated
  9. customthe residue purified by preparative silica gel chromatography

Sources & evidence

ORD record
ord-d30630e92a6f4ceb8a810357af69fcf7
Source dataset
uspto-grants-2010_01
Patent number
US07642267B2

Reaction notes

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