Reaction #46453

Reaction equation

H2O

Sec BuLi

3-benzyl-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-indole-1-carboxylic acid tert-butyl ester

dimethyl sulfide

→

3-benzyl-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-2-methylsulfanyl-indole-1-carboxylic acid tert-butyl ester

Solvents

THF

Conditions

Workup

1. 1
   Temperatureto warm up to room temperature for 30 minutes
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with water and brine
4. 4
   DryingAfter drying over MgSO4
5. 5
   Concentrationthe organic fraction was concentrated in vacuo

Procedure

A solution of 3-benzyl-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-indole-1-carboxylic acid tert-butyl ester (186 mg, 0.38 mmol) in THF (5 ml) was cooled to −78° C., and Sec-BuLi (1.4 ml, 1.4 M in cyclohexane) was added. After stirring at −78° C. for 20 minutes, 1 ml of dimethyl sulfide was added and the reaction was allowed to warm up to room temperature for 30 minutes. H2O was slowly added, followed by EtOAC. The organic layer was separated and washed with water and brine. After drying over MgSO4, the organic fraction was concentrated in vacuo to give crude 3-benzyl-7-(4-tert-butoxycarbonyl-piperazin-1-yl)-2-methylsulfanyl-indole-1-carboxylic acid tert-butyl ester as an oil (277 mg), which was used without further purification.

Source