Reaction #68402

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

i-PrCOCl

→

title compound

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

Solvents

EtOAc

CH2Cl2

Conditions

Workup

1. 1
   Washwashed with aqueous Na2CO3 and 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

To a solution of 6-amino-1-benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-1H-indole-3-carboxamide (Compound 125, 18 mg, 0.042 mmol) in CH2Cl2 (1 ml) was added i-PrCOCl (8.7 μl, 0.089 mmol) and DMAP (10 mg, 0.089 mmol). The reaction was stirred at room temperature for 2 h, diluted with EtOAc, washed with aqueous Na2CO3 and 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