反応 #48827

反応方程式

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

triethylamine

→

oil

収率 39.0%

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

収率 39.0%

溶媒

DCM

反応条件

後処理

1. 1
   その他for 7 hours
2. 2
   その他Reaction mixture
3. 3
   ろ過filtered through diatomaceous earth
4. 4
   洗浄was washed with DCM (×3)
5. 5
   濃縮Filtrate concentrated in vacuo
6. 6
   洗浄washed with 1M hydrochloric acid, saturated sodium hydrogen carbonate, saturated brine
7. 7
   乾燥dried (MgSO4)
8. 8
   ろ過Filtered
9. 9
   濃縮filtrate concentrated in vacuo
10. 10
    その他chromatographed (0-50% ethyl acetate/isohexane)

実験手順

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%).

出典