Reaktion #166602

Reaktionsgleichung

sodium bicarbonate

4-Fluoropyridin-2-amine

ethanol

ethyl 2-chloro-3-oxopropanoate

→

ethyl 7-fluoroimidazo[1,2-a]pyridine-3-carboxylate

Lösungsmittel

ethyl acetate

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool the solvent
2. 2
   Sonstigewas removed under vacuum
3. 3
   Sonstigeto give a brown solid
4. 4
   workup.DISSOLUTIONto dissolve
5. 5
   SonstigeThe phases were separated
6. 6
   Extraktionthe bicarbonate solution was extracted further with ethyl acetate (75 mL)
7. 7
   TrocknenThe combined ethyl acetate extracts were dried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated under vacuum
10. 10
    Sonstigeto give a solid
11. 11
    Wascheneluting with ethyl acetate
12. 12
    workup.ADDITIONFractions containing the product
13. 13
    Einengenwere concentrated

Vorschrift

4-Fluoropyridin-2-amine (10.0 g, 48.0 mmol) was mixed with ethanol (40 mL) in a reaction flask, under an atmosphere of dry nitrogen. A solution of ethyl 2-chloro-3-oxopropanoate (5% in benzene, 178 mL, Commercial solution from Toronto Research Chemicals Inc.) was added. The mixture was heated to 60° C. under nitrogen for 4 hours. After allowing the mixture to cool the solvent was removed under vacuum to give a brown solid. The solid was mixed with ethyl acetate (300 mL) and sodium bicarbonate solution (75 mL) and stirred to dissolve. The phases were separated and the bicarbonate solution was extracted further with ethyl acetate (75 mL). The combined ethyl acetate extracts were dried over sodium sulfate, filtered and concentrated under vacuum to give a solid. The crude material was dissolved in ethyl acetate and passed through a short column of silica, eluting with ethyl acetate. Fractions containing the product were concentrated to give ethyl 7-fluoroimidazo[1,2-a]pyridine-3-carboxylate as a white solid (13 g).

Quelle