Reacción #745660

Ecuación de reacción

dimethylhydroxylamine HCl

triethylamine

4-chloropyridine-2-carbonyl chloride hydrochloride

→

4-chloro-N-methoxy-N-methylpyridine-2-carboxamide

Rendimiento 98.0%

Disolventes

THF

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITat RT for 16 h
2. 2
   OtroThe solvent was removed under reduced pressure
3. 3
   Otropartitioned between EtOAc and water
4. 4
   LavadoThe organic layer was washed with H2O and brine
5. 5
   Secadodried over Na2SO4
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe crude product was purified by MPLC (biotage)
8. 8
   Lavadoeluted with 30% EtOAc/Hex

Procedimiento

To a mixture of dimethylhydroxylamine HCl (510 mg, 5.18 mmol) and triethylamine (2.16 mL, 15.5 mmol) in anhydrous THF (9.41 mL) and acetonitrile (2.35 mL) was added 4-chloropyridine-2-carbonyl chloride hydrochloride (1.00 g, 4.71 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 2 h then at RT for 16 h. The solvent was removed under reduced pressure and partitioned between EtOAc and water. The organic layer was washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by MPLC (biotage) eluted with 30% EtOAc/Hex to afford 925 mg (98%) of 4-chloro-N-methoxy-N-methylpyridine-2-carboxamide as an orange oil: TLC (50% EtOAc/Hex), Rf=0.31.

Fuente