반응 #3118

반응 방정식

1-Acetyl-6-bromo-5-hydroxyindoline

methyl 2-chloro-2,2-difluoroacetate

methyl 2-chloro-2,2-difluoroacetate

potassium carbonate

potassium carbonate

→

title compound

1-Acetyl-6-bromo-5-difluoromethoxyindoline

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타placed in a 65° C.
2. 2
   온도heated for 18 hr
3. 3
   기타The solvent was then removed in vacuo
4. 4
   기타the residue was partitioned between cold 3N HCl and ether
5. 5
   추출The aqueous layer was extracted three times with ether
6. 6
   세척the combined organic extracts were washed with brine
7. 7
   건조dried (Na2SO4)
8. 8
   여과filtered
9. 9
   기타evaporated
10. 10
    기타The solid was purified by flash chromatography (2% MeOH/CH2Cl2)

실험 절차

1-Acetyl-6-bromo-5-hydroxyindoline (2 g, 7.8 mmol), methyl 2-chloro-2,2-difluoroacetate (0.82 ml, 7.8 mmol) and potassium carbonate (1.08 g, 7.8 mmol) were suspended in N,N-dimethylformamide (20 mL) under an argon atmosphere and placed in a 65° C. oil bath. After 3 hr, additional methyl 2-chloro-2,2-difluoroacetate (0.3 ml, 2.8 mmol) and potassium carbonate (0.3 g, 2.2 mmol) was added and heated for 18 hr. The solvent was then removed in vacuo and the residue was partitioned between cold 3N HCl and ether. The aqueous layer was extracted three times with ether, the combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated. The solid was purified by flash chromatography (2% MeOH/CH2Cl2) to provide the title compound as a white solid

출처