Tributylvinyltin → 5-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-vinyl-1H-benzoimidazole

HRID 1661927Notes

Reaction equation

HRID 1661927 reaction equation
[CH2:1]([C:8]1[CH:29]=[C:28]([O:30][CH3:31])[C:11]2[N:12]([CH2:24][CH2:25][O:26][CH3:27])[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=3)=[N:14][C:10]=2[C:9]=1I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC>C1COCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([C:8]1[CH:29]=[C:28]([O:30][CH3:31])[C:11]2[N:12]([CH2:24][CH2:25][O:26][CH3:27])[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=3)=[N:14][C:10]=2[C:9]=1[CH:33]=[CH2:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 113532215-Benzyl-4-iodo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

Product 1

HCID 577720835-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-4-vinyl-1H-benzoimidazole

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 300 mg (0.556 mmol) 5-benzyl-4-iodo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole, 40 mg bis(triphenylphosphine) palladium (II) dichloride and 0.2 ml tributyl(vinyl)stannane in 3 ml THF is stirred at reflux temperature for 24 h. The reaction mixture is concentrated in vacuo and the residue is purified by flash-chromatography on silica gel (hexane:EtOAc=6:1) to afford 278 mg of the title compound as a yellow crystalline solid.

Workup

  1. temperatureat reflux temperature for 24 h
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=6:1)

Sources & evidence

ORD record
ord-09c472fc1a554fec99123caa53a4dee4
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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