反応 #49033

反応方程式

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

溶媒

EtOAc

MeOH

反応条件

後処理

1. 1
   その他the solvent was evaporated
2. 2
   workup.ADDITIONThe resultant residue was added to THF/H2O
3. 3
   洗浄the organic layer was washed with 0.4 N aqueous HCl
4. 4
   乾燥dried over Na2SO4
5. 5
   その他evaporated
6. 6
   その他The resultant residue was purified by silica gel chromatography (CH2Cl2/MeOH as a developing solvent)

実験手順

(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).

出典