Reaktion #49033

Reaktionsgleichung

tetrabutylammonium fluoride

(E)-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-2-methyl-propoxyimino)-methyl]-benzamide

triphenylphosphine-3,3′,3″-trisulfonic acid trisodium salt

N(iPr)2Et

trimethylsilyl acetylene

→

title compound

(E)-2-(4-Ethynyl-2-fluoro-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-2-m ethyl-propoxyimino)-methyl]-benzamide

Lösungsmittel

EtOAc

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was evaporated
2. 2
   workup.ADDITIONThe resultant residue was added to THF/H2O
3. 3
   Waschenthe organic layer was washed with 0.4 N aqueous HCl
4. 4
   Trocknendried over Na2SO4
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe resultant residue was purified by silica gel chromatography (CH2Cl2/MeOH as a developing solvent)

Vorschrift

(E)-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-2-methyl-propoxyimino)-methyl]-benzamide (200 mg, 0.35 mmol), Pd(CH3CN)2Cl2 (4.5 mg, 0.0176 mmol), triphenylphosphine-3,3′,3″-trisulfonic acid trisodium salt (25.0 mg, 0.037 mmol), N(iPr)2Et (48.0 mg, 0.37 mmol), trimethylsilyl acetylene (172 mg, 1.76 mmol), and CuI (3.4 mg, 0.0176 mmol) were stirred in MeOH at room temperature for 1 hour, and the solvent was evaporated. The resultant residue was added to THF/H2O containing tetrabutylammonium fluoride (0.35 mmol), and the mixture was stirred for 1 hour. EtOAc was added thereto, and the organic layer was washed with 0.4 N aqueous HCl, dried over Na2SO4, and evaporated. The resultant residue was purified by silica gel chromatography (CH2Cl2/MeOH as a developing solvent) to give a title compound (99 mg).

Quelle