Reaktion #171975

Reaktionsgleichung

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

1-methyl-1H-indol-4-amine

BINAP

K2CO3

→

tert-butyl (1S,2R)-2-(4-cyano-3-(1-methyl-1H-indol-4-ylamino)phenylamino)cyclohexylcarbamate

Ausbeute 39.5%

Lösungsmittel

dioxane

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 5% NaHCO3, dried over Na2SO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by a silica gel column
8. 8
   Wascheneluted with 10-40% EtOAc in hexane

Vorschrift

A mixture of tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate (200 mg, 0.507 mmol), 1-methyl-1H-indol-4-amine (160 mg, 1.09 mmol), BINAP (50 mg, 0.080 mmol), Pd(OAc)2 (25 mg, 0.11 mmol) and K2CO3 (150 mg, 1.08 mmol) in dioxane (4 mL) was degassed with Ar, then was stirred at 100 C for 16 h. EtOAc and water were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with 10-40% EtOAc in hexane to give tert-butyl (1S,2R)-2-(4-cyano-3-(1-methyl-1H-indol-4-ylamino)phenylamino)cyclohexylcarbamate (92 mg) as an oil.

Quelle