Reaction #68403

Reaction equation

6-amino-1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide

Compound 125

6-amino-1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide

ethyl4-bromobutanoate

→

title compound

1-Benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-6-(2-oxopyrrolidin-1-yl)-1H-indole-3-carboxamide

Solvents

NMP

EtOAc

Conditions

Workup

1. 1
   Washwashed with brine
2. 2
   Dryingdried over Na2SO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   OtherThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Procedure

A solution of 6-amino-1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide (Compound 125, 20 mg, 0.046 mmol) and ethyl4-bromobutanoate (13 μl, 0.092 mmol) in NMP (1 ml) was heated at 168° C. for 16 h, cooled to room temperature, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound.

Source