반응 #171975

반응 방정식

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

수율 39.5%

용매

dioxane

반응 조건

후처리

1. 1
   기타was degassed with Ar
2. 2
   workup.ADDITIONEtOAc and water were added
3. 3
   기타The organic phase was separated
4. 4
   세척washed with 1N HCl
5. 5
   건조with 5% NaHCO3, dried over Na2SO4
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue was purified by a silica gel column
8. 8
   세척eluted with 10-40% EtOAc in hexane

실험 절차

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.

출처