Reaktion #171974

Reaktionsgleichung

tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate

m-toluidine

BINAP

Cs2CO3

→

tert-butyl (1S,2R)-2-(4-cyano-3-(m-tolylamino)phenylamino)cyclohexylcarbamate

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed with Ar
2. 2
   workup.ADDITIONEtOAc and water were added
3. 3
   SonstigeThe organic phase was separated
4. 4
   Waschenwashed with 1N HCl
5. 5
   Trocknenwith brine, dried over Na2SO4
6. 6
   Einengenconcentrated in vacuo

Vorschrift

A mixture of tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate (98 mg, 0.25 mmol), m-toluidine (54 uL, 0.50 mmol), BINAP (31 mg, 0.050 mmol), Pd(OAc)2 (12 mg, 0.053 mmol) and Cs2CO3 (160 mg, 0.49 mmol) in toluene (3 mL) was degassed with Ar, then was stirred at 100 C for 3 h. EtOAc and water were added. The organic phase was separated, washed with 1N HCl, then with brine, dried over Na2SO4, concentrated in vacuo to give tert-butyl (1S,2R)-2-(4-cyano-3-(m-tolylamino)phenylamino)cyclohexylcarbamate as a residue.

Quelle