반응 #45543

반응 방정식

4-bromo-2-(2,2-dimethylpropionylamino)-5-iodo-3-methoxy-6-methylbenzamide

trifluoromethanesulfonic acid anhydride

hydrochloric acid

→

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide

용매

pyridine

반응 조건

후처리

1. 1
   기타the reaction liquid
2. 2
   추출followed by extraction with ethyl acetate (200 ml×2)
3. 3
   세척The organic layer was washed successively with 1 N hydrochloric acid (200 ml×2), saturated sodium bicarbonate water (50 ml), saturated brine (50 ml)
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타the residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1)
7. 7
   기타to obtain the entitled compound (1.86 g, quant.) as a pale yellow solid

실험 절차

4-Dimethylaminopyridine (54.2 mg, 443 μmol) was added to a pyridine (40 ml) suspension of 4-bromo-2-(2,2-dimethylpropionylamino)-5-iodo-3-methoxy-6-methylbenzamide (I-5) (2.08 g, 4.43 mmol), followed by cooling at 0° C. To this, trifluoromethanesulfonic acid anhydride (2.25 ml, 13.3 mmol) was dropwise added, followed by stirring at room temperature for 2.5 hours, the reaction liquid was put into 1 N hydrochloric acid (200 ml), followed by extraction with ethyl acetate (200 ml×2). The organic layer was washed successively with 1 N hydrochloric acid (200 ml×2), saturated sodium bicarbonate water (50 ml), saturated brine (50 ml), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified twice by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the entitled compound (1.86 g, quant.) as a pale yellow solid.

출처