Reaction #68397

Reaction equation

N-(2-(3-methylbut-1-ynyl)-5-nitrophenyl)butyramide

Compound 119

N-(2-(3-methylbut-1-ynyl)-5-nitrophenyl)butyramide

KOt-Bu

→

title compound

2-Isopropyl-6-nitro-1H-indole

Solvents

NMP

EtOAc

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   Washwashed with brine
3. 3
   Dryingdried over Na2SO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   OtherThe residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes)

Procedure

To a solution of N-(2-(3-methylbut-1-ynyl)-5-nitrophenyl)butyramide (Compound 119, 900 mg, 3.29 mmol) in NMP (10 ml) was added KOt-Bu (552 mg, 4.94 mmol) and the mixture was stirred at 70° 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→25% EtOAc-hexanes) to yield the title compound.

Source