Reaction #68373

Reaction equation

hydrazine

1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylic acid

Compound 56

1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylic acid

EDC

→

title compound

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

Solvents

EtOAc

CH2Cl2

Conditions

Workup

1. 1
   Washwashed with H2O, brine
2. 2
   Dryingdried over Na2SO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   OtherThe residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes)

Procedure

Following General Procedure E, 1-benzyl-3-(3,4-difluorobenzylcarbamoyl)-2-isopropyl-1H-indole-6-carboxylic acid (Compound 56, 82 mg, 0.176 mmol) in CH2Cl2 (8 ml) was added EDC (51 mg, 0.264 mmol) and DMAP (26 mg, 0.256 mmol), followed by hydrazine (7 mg, 0.264 mmol). The reaction was stirred at room temperature for 12 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes) to yield the title compound as a yellow oil.

Source