تفاعل #49033

معادلة التفاعل

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

المذيبات

EtOAc

MeOH

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

(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).

المصدر