反応 #172089

反応方程式

(R)-tert-butyl 1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamate

pyridine-2-boronic acid pinacol ester

Cs2CO3

→

(R)-tert-butyl 1-amino-1-oxo-3-(4-(pyridin-2-yl)phenyl)propan-2-ylcarbamate

収率 33.5%

溶媒

DMF

反応条件

後処理

1. 1
   その他was degassed with argon
2. 2
   workup.ADDITIONWater and EtOAc were added
3. 3
   その他The organic phase was separated
4. 4
   乾燥dried over Na2SO4
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The residue was purified by a silica gel column, which
7. 7
   洗浄was eluted with 20-100% EtOAc in hexane

実験手順

A mixture of (R)-tert-butyl 1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamate (970 mg, 2.48 mmol), pyridine-2-boronic acid pinacol ester (505 mg, 2.46 mmol), dppf (275 mg, 0.496 mmol), Cs2CO3 (1.00 g, 3.06 mmol), Pd(OAc)2 (56 mg, 0.249 mmol) and CuCl (25 mg, 0.252 mmol) in DMF (10 mL) was degassed with argon, then was stirred at 100 C for 18 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, which was eluted with 20-100% EtOAc in hexane to give (R)-tert-butyl 1-amino-1-oxo-3-(4-(pyridin-2-yl)phenyl)propan-2-ylcarbamate (281 mg).

出典