Tributylvinyltin → 4-(Ethenyl)-2-[(4-chlorophenoxy)methyl]-1-trifluoromethanesulfonylbenzimidazole

HRID 1384005Notes

Reaction equation

HRID 1384005 reaction equation
FC(F)(F)S(O[C:7]1[C:15]2[N:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:12]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[C:11]=2[CH:10]=[CH:9][CH:8]=1)(=O)=O.[Cl-].[Li+].[CH:36]([Sn](CCCC)(CCCC)CCCC)=[CH2:37]>O1CCCC1.[Pd].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:36]([C:7]1[C:15]2[N:14]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[N:12]([S:25]([C:28]([F:29])([F:31])[F:30])(=[O:27])=[O:26])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[CH2:37]

Participants

7

Reactant 3

HCID 81998Tributylvinyltin2×HCID 433294Lithium ChlorideHCID 211887374-Trifluoromethanesulfonyloxy-2-[(4-chlorophenoxy)methyl]-1-trifluoromethanesulfonylbenzimidazole

Product 1

HCID 211886134-(Ethenyl)-2-[(4-chlorophenoxy)methyl]-1-trifluoromethanesulfonylbenzimidazole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a 250 ml single neck round bottom flask, under a nitrogen atmosphere, were added 4-trifluoromethanesulfonyloxy-2-[(4-chlorophenoxy)methyl]-1-trifluoromethanesulfonylbenzimidazole (5.00 g, 9.28 mmol), lithium chloride (1.18 g, 27.84 mmol), vinyltributyltin (4.12 g, 12.99 mmol), and bis(triphenylphosphine)palladium(II) chloride (303 mg, 0.371 mmol) in anhydrous tetrahydrofuran (99 ml). The resulting mixture was stirred for five hours at reflux, followed by the addition of an additional 0.15 mg of the palladium catalyst. The contents were then stirred overnight. The progress of the reaction was monitored by thin layer chromatography. An additional 0.15 mg of the palladium catalyst and 0.5 ml of vinyltributyltin were added to the reaction mixture and it was refluxed for five hours. The desired title product was further purified by flash chromatography.

Workup

  1. temperatureat reflux
  2. stirringThe contents were then stirred overnight
  3. temperaturewas refluxed for five hours
  4. customThe desired title product was further purified by flash chromatography

Sources & evidence

ORD record
ord-aa0148f3364b4eeea0c9f7dde13582bd
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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