Reaktion #3118

Reaktionsgleichung

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

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeplaced in a 65° C.
2. 2
   Temperaturheated for 18 hr
3. 3
   SonstigeThe solvent was then removed in vacuo
4. 4
   Sonstigethe residue was partitioned between cold 3N HCl and ether
5. 5
   ExtraktionThe aqueous layer was extracted three times with ether
6. 6
   Waschenthe combined organic extracts were washed with brine
7. 7
   Trocknendried (Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe solid was purified by flash chromatography (2% MeOH/CH2Cl2)

Vorschrift

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

Quelle