Allyltributylstannane → 4-(Prop-2-enyl)-2-[(4-chlorophenoxy)methyl]-1-trifluoromethanesulfonylbenzimidazole

HRID 1384004Notes

Reaction equation

HRID 1384004 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+].[CH2:36]([Sn](CCCC)(CCCC)CCCC)[CH:37]=[CH2:38]>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>[CH2:38]([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:26])=[O:27])[C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH:37]=[CH2:36]

Participants

7

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 211887374-Trifluoromethanesulfonyloxy-2-[(4-chlorophenoxy)methyl]-1-trifluoromethanesulfonylbenzimidazole

Product 1

HCID 211884814-(Prop-2-enyl)-2-[(4-chlorophenoxy)methyl]-1-trifluoromethanesulfonylbenzimidazole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 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 (4.97 g, 9.22 mmol), lithium chloride (1.17 g, 27.65 mmol), allyltributyltin (4.27 g, 12.90 mmol), and bis(triphenylphosphine)palladium(II) chloride (301.03 mg, 0.369 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. The desired title product was further purified by flash chromatography.

Workup

  1. temperatureat reflux
  2. stirringThe contents were then stirred overnight
  3. customThe desired title product was further purified by flash chromatography

Sources & evidence

ORD record
ord-6875cbaa5b3b4a18944bf9e735b38405
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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