반응 #172089

반응 방정식

(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

수율 33.5%

용매

DMF

반응 조건

후처리

1. 1
   기타was degassed with argon
2. 2
   workup.ADDITIONWater and EtOAc were added
3. 3
   기타The organic phase was separated
4. 4
   건조dried over Na2SO4
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by a silica gel column, which
7. 7
   세척was eluted with 20-100% EtOAc in hexane

실험 절차

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).

출처