Reacción #45257

Ecuación de reacción

solution

ethyl 3-{3-tert-butyl-5-[3-(4-chlorophenyl)ureido]-1H-pyrazol-1-yl}benzoate

methyl magnesium bromide

toluene THF

→

1-{5-t-butyl-2-[3-(1-hydroxy-1-methyl-ethyl)-phenyl]-2H-pyrazol-3-yl}-3-(4-chloro-phenyl)-urea

Rendimiento 81.5%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto rise to RT
2. 2
   workup.STIRRINGstirred for another 2 h
3. 3
   OtroThe reaction mixture was quenched with saturated NH4Cl and aqueous HCl solution (10%)
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe combined organic extracts were washed with brine
6. 6
   Secadodried (Na2SO4)
7. 7
   Otrothe solvent was removed in vacuo
8. 8
   Otrothe residue was purified by column chromatography

Procedimiento

To a solution of Example C (220 mg, 0.5 mmol) in dry THF (20 mL) was added dropwise a solution of methyl magnesium bromide in toluene/THF (3.6 mL, 5.0 mmol) at −78° C. under N2. After stirring for 1 h, the mixture was allowed to rise to RT and stirred for another 2 h. The reaction mixture was quenched with saturated NH4Cl and aqueous HCl solution (10%), and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), the solvent was removed in vacuo and the residue was purified by column chromatography to afford 1-{5-t-butyl-2-[3-(1-hydroxy-1-methyl-ethyl)-phenyl]-2H-pyrazol-3-yl}-3-(4-chloro-phenyl)-urea (174 mg, 81%). 1H NMR (DMSO-d6): 9.11 (s, 1H), 8.34 (s, 1H), 7.59 (s, 1H), 7.46 (t, J=8.8 Hz, 1H), 7.43-7.40 (m, 3H), 7.31-7.28 (m, 3H), 6.34 (s, 1H), 5.13 (s, 1H), 1.42 (s, 6H), 1.27 (s, 9H); MS (ESI) m/z: 428 (M+H+).

Fuente