Reacción #48827

Ecuación de reacción

tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

triethylamine

→

oil

Rendimiento 39.0%

tert-Butyl 3-({3-[4-(ethoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

Rendimiento 39.0%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofor 7 hours
2. 2
   OtroReaction mixture
3. 3
   Filtraciónfiltered through diatomaceous earth
4. 4
   Lavadowas washed with DCM (×3)
5. 5
   ConcentraciónFiltrate concentrated in vacuo
6. 6
   Lavadowashed with 1M hydrochloric acid, saturated sodium hydrogen carbonate, saturated brine
7. 7
   Secadodried (MgSO4)
8. 8
   FiltraciónFiltered
9. 9
   Concentraciónfiltrate concentrated in vacuo
10. 10
    Otrochromatographed (0-50% ethyl acetate/isohexane)

Procedimiento

tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate (391 mg, 1 mmol), ethyl-4-boronic acid benzoate (388 mg, 2.0 equiv), copper (II) acetate (363 mg, 2.0 equiv) and triethylamine (0.7 mL; 5.0 equiv) were suspended in dry DCM over freshly activated powdered 4A molecular sieves (ca. 1 g) for 7 hours under an ambient atmosphere. Reaction mixture filtered through diatomaceous earth was washed with DCM (×3). Filtrate concentrated in vacuo, taken up in ethyl acetate and washed with 1M hydrochloric acid, saturated sodium hydrogen carbonate, saturated brine and dried (MgSO4). Filtered, filtrate concentrated in vacuo and chromatographed (0-50% ethyl acetate/isohexane) to give a brown oil (210 mg, 39%).

Fuente