Reaction #68374

Reaction equation

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

Compound 88

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

triethyl orthoformate

→

title compound

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

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   OtherThe residue was purified by chromatography on silica gel (0→55% EtOAc-hexanes)

Procedure

1-benzyl-N-(3,4-difluorobenzyl)-6-(hydrazinecarbonyl)-2-isopropyl-1H-indole-3-carboxamide (Compound 88, 21 mg, 0.044 mmol) in triethyl orthoformate (5 ml) was heated to 145° C. for 5 h, then concentrated in vacuo. The residue was purified by chromatography on silica gel (0→55% EtOAc-hexanes) to yield the title compound as a white solid.

Source