反応 #45257

反応方程式

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

収率 81.5%

溶媒

THF

反応条件

後処理

1. 1
   その他to rise to RT
2. 2
   workup.STIRRINGstirred for another 2 h
3. 3
   その他The reaction mixture was quenched with saturated NH4Cl and aqueous HCl solution (10%)
4. 4
   抽出extracted with ethyl acetate
5. 5
   洗浄The combined organic extracts were washed with brine
6. 6
   乾燥dried (Na2SO4)
7. 7
   その他the solvent was removed in vacuo
8. 8
   その他the residue was purified by column chromatography

実験手順

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+).

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