反応 #171975

反応方程式

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

収率 39.5%

溶媒

dioxane

反応条件

後処理

1. 1
   その他was degassed with Ar
2. 2
   workup.ADDITIONEtOAc and water were added
3. 3
   その他The organic phase was separated
4. 4
   洗浄washed with 1N HCl
5. 5
   乾燥with 5% NaHCO3, dried over Na2SO4
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The residue was purified by a silica gel column
8. 8
   洗浄eluted with 10-40% EtOAc in hexane

実験手順

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.

出典