Reacción #970270

Ecuación de reacción

2,5-difluorobenzoic acid

EDCI

NH2NHBoc

TFA

→

desired crude product

2,5-difluorobenzoic acid hydrazide

Disolventes

THF DMF

DCM

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction was quenched with water (30 mL)
2. 2
   workup.ADDITIONdiluted with EtOAc (30 mL)
3. 3
   LavadoThe organic layer was then washed with HCl (0.5 M, 20 mL), saturated NaHCO3 (20 mL), and brine (20 mL)
4. 4
   SecadoThe organic layer was then dried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   Otroto afford the crude Boc-protected product, which
8. 8
   workup.STIRRINGAfter stirring for 2 hours
9. 9
   Concentraciónthe reaction mixture was concentrated
10. 10
    workup.DISSOLUTIONthe residue was dissolved in DCM (60 mL)
11. 11
    LavadoThe solution was washed with saturated NaHCO3 (40 mL)
12. 12
    Secadodried over Na2SO4
13. 13
    Filtraciónfiltered
14. 14
    Concentraciónconcentrated under reduced pressure

Procedimiento

To a solution of 2,5-difluorobenzoic acid (3.5 g, 22 mmol) in THF/DMF (20 mL/20 mL) was added EDCI (4.7 g, 24 mmol), DMAP (50 mg) and NH2NHBoc (3.07 g, 23.2 mmol). After stirring for 16 hours, the reaction was quenched with water (30 mL) and diluted with EtOAc (30 mL). The organic layer was then washed with HCl (0.5 M, 20 mL), saturated NaHCO3 (20 mL), and brine (20 mL). The organic layer was then dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude Boc-protected product, which was then dissolved in DCM (60 mL) at 0° C. TFA (50 mL) was added to the above DCM solution. After stirring for 2 hours, the reaction mixture was concentrated and the residue was dissolved in DCM (60 mL). The solution was washed with saturated NaHCO3 (40 mL) and dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired crude product.

Fuente