반응 #49003

반응 방정식

3,4-difluoro-2-(2-fluoro-4-trimethylsilanylethynyl-phenylamino)-N-(2-hydroxy-ethoxy)-5-(2-hydroxy-ethoxymethyl)-benzamide

tetra-n-butylammonium fluoride

→

2-(4-ethynyl-2-fluoro-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-5-(2-hydroxy-ethoxymethyl)-benzamide

수율 68.2%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITION0.1 N Hydrochloric acid was added to the resultant residue
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   세척The combined organic layers were washed with 0.1 N hydrochloric acid and saturated brine
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The resultant residue was purified by silica gel column chromatography (Presep Silica Gel Type S (Wako Pure Chemical Industries), 10 g, CH2Cl2/MeOH (10:1 to 5:1))

실험 절차

To a solution of the resultant 3,4-difluoro-2-(2-fluoro-4-trimethylsilanylethynyl-phenylamino)-N-(2-hydroxy-ethoxy)-5-(2-hydroxy-ethoxymethyl)-benzamide (37.6 mg) in tetrahydrofuran (anhydrous, 1.0 ml) was added tetra-n-butylammonium fluoride (1 M solution in THF, 113 μL, 113 μmol) at room temperature, and the mixture was stirred for 3 hours. The reaction mixture was concentrated under reduced pressure. 0.1 N Hydrochloric acid was added to the resultant residue, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with 0.1 N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (Presep Silica Gel Type S (Wako Pure Chemical Industries), 10 g, CH2Cl2/MeOH (10:1 to 5:1)) to give 2-(4-ethynyl-2-fluoro-phenylamino)-3,4-difluoro-N-(2-hydroxy-ethoxy)-5-(2-hydroxy-ethoxymethyl)-benzamide (21.9 mg, 68%) as a yellow powder.

출처