Reacción #48829

Ecuación de reacción

water

Potassium carbonate

3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide

1-chloro-4,5-difluoro-2-(methylsulfonyl)benzene

→

desired compound

Rendimiento 49.5%

3-[5-Chloro-2-fluoro-4-(methylsulfonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Rendimiento 49.5%

Disolventes

NMP

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITleft
2. 2
   Temperaturato cool
3. 3
   Extracciónextracted with ethyl acetate (2×150 mL)
4. 4
   LavadoThe combined organics were washed with water, brine
5. 5
   Secadodried (MgSO4)
6. 6
   Otrobefore evaporation in vacuo
7. 7
   LavadoChromatography on silica, eluting with 0 to 10% methanol in ethyl acetate

Procedimiento

Potassium carbonate (1.00 g) was added to a solution of 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide (1.41 g) and 1-chloro-4,5-difluoro-2-(methylsulfonyl)benzene (0.79 g) in NMP (20 mL). The mixture was heated to 115° C. for 3.5 hours and left to cool before being poured into water (300 mL) and extracted with ethyl acetate (2×150 mL). The combined organics were washed with water, brine and dried (MgSO4) before evaporation in vacuo. Chromatography on silica, eluting with 0 to 10% methanol in ethyl acetate, afforded the desired compound (0.86 g)

Fuente