Reacción #1563936

Ecuación de reacción

K2CO3

1-amino-4-((tert-butoxycarbonyl)amino)-3-fluoropyridin-1-ium 2,4-dinitrophenolate

Ethyl propiolate

→

title compound

Ethyl 5-((tert-butoxycarbonyl)amino)-4-fluoropyrazolo[1,5-a]pyridine-3-carboxylate

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued at 28° C. for 16 hr
3. 3
   OtroReaction mixture
4. 4
   Filtraciónwas filtered
5. 5
   Otroto remove the salt, filtrate
6. 6
   Otrocollected
7. 7
   workup.ADDITIONwas diluted with EtOAc
8. 8
   Lavadowashed it with water
9. 9
   Secadodried over anhydrous sodium sulphate
10. 10
    Concentraciónconcentrated under reduced pressure
11. 11
    Otroto afford crude
12. 12
    OtroThe crude obtained
13. 13
    Otrowas purified by column purification (using 60-120 silicagel and 10% EtOAc in Hexane as eluant)

Procedimiento

K2CO3 (36.96 g, 267 mmol) was added to a solution of 1-amino-4-((tert-butoxycarbonyl)amino)-3-fluoropyridin-1-ium 2,4-dinitrophenolate (50 g, 121 mmol) in THF (500 mL) at 28° C. and continued stirring at same temperature for 30 min. Ethyl propiolate (14.3 g, 145 mmol) was added to above solution and stirring was continued at 28° C. for 16 hr. Reaction mixture was filtered to remove the salt, filtrate collected was diluted with EtOAc washed it with water followed by brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford crude. The crude obtained was purified by column purification (using 60-120 silicagel and 10% EtOAc in Hexane as eluant) to afford the title compound.

Fuente