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

To a 250 ml round bottom flask were added 4-trifluoromethanesulfonyloxy-2-[(4-chlorophenoxy)methyl]-1-trifluoromethanesulfonylbenzimidazole (5.00 g, 9.28 mmol), palladium tetrakis(triphenylphosphine) (428 mg, 0.371 mmol), lithium chloride (2.95 g, 69.6 mmol) and vinyltributyltin (2.94 g, 9.28 mmol) to anhydrous tetrahydrofuran. The reaction mixture was heated to reflux and maintained at this temperature overnight. The progress of the reaction was monitored by thin layer chromatography. An additional 428 mg of the palladium catalyst was added and the resulting mixture was refluxed an additional three hours. To the reaction mixture was added cuprous iodide (35.3 mg, 0.02 eq) and the reaction mixture was refluxed overnight. The solvents were removed in vacuo. The residue was redissolved in ethyl acetate (500 ml) and was washed with 1:1 water:28% aqueous ammonium hydroxide (3×). The organic fraction was dried over sodium sulfate. The desired title product was further purified by column chromatography.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux
3. temperaturemaintained at this temperature overnight
4. temperaturethe resulting mixture was refluxed an additional three hours
5. temperaturethe reaction mixture was refluxed overnight
6. customThe solvents were removed in vacuo
7. dissolutionThe residue was redissolved in ethyl acetate (500 ml)
8. washwas washed with 1:1 water
9. dry with materialThe organic fraction was dried over sodium sulfate
10. customThe desired title product was further purified by column chromatography

ORD-Eintrag

ord-1cca125557ba4df5a96811379e929188

Quelldatensatz

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06255494B1