Reaktion #46439

Reaktionsgleichung

1-Benzyl-4-bromo-1H-indole-2-carboxylic acid benzyl ester

1-methyl-piperazine

Cs2CO3

→

1-benzyl-4-(4-methyl-piperazin-1-yl)-1H-indole-2-carboxylic acid benzyl ester

Ausbeute 71.0%

Lösungsmittel

Dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   FiltrationThe reaction mixture was filtered through celite
3. 3
   Waschenwashed with ethyl acetate
4. 4
   EinengenThe filtrate was concentrated in vacuo
5. 5
   Sonstigethe resulting brown residue was purified by preparative TLC (7% MeOH in CH2Cl2 containing 0.7% NH4OH)

Vorschrift

A solution of 1-Benzyl-4-bromo-1H-indole-2-carboxylic acid benzyl ester (235 mg, 0.56 mmol) and 1-methyl-piperazine (80 ul, 0.72 mmol) in 5 ml Dioxane was added to a mixture of Pd2(dba)3 (10 mg, 0.01 mmol), BINAP (18 mg, 0.03 mmol), Cs2CO3 (547 mg, 1.68 mmol). With stirring, the solution was heated at 100° C. overnight and was allowed to cool to room temperature. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resulting brown residue was purified by preparative TLC (7% MeOH in CH2Cl2 containing 0.7% NH4OH) to give 174 mg of 1-benzyl-4-(4-methyl-piperazin-1-yl)-1H-indole-2-carboxylic acid benzyl ester as a yellow solid (71%). MS: (M+H)+ 440.3.

Quelle