Reaktion #172089

Reaktionsgleichung

(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

Ausbeute 33.5%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle