Dimethylformamide → N-[2-(5-allyloxyindol-3-yl)ethyl]propionamide

HRID 1636603Notes

Reaction equation

[CH2:1](Br)[CH:2]=[CH2:3].[OH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 50 °C

Procedure

Allyl bromide (11 g, 90.8 mmol.) was added, under argon atmosphere, to a mixture of N-[2-(5-hydroxyindol-3-yl)ethyl]propionamide (20.0 g, 92.5 mmol.), cesium carbonate (31.6 g, 97 mmol.) and N,N-dimethylformamide (150 mL) at 0° C. The reaction mixture was stirred for one hour at 50° C., to which was added water. The product was extracted with ethyl acetate. The extract solution was washed with water and dried. The solvent was then distilled off to leave the title compound (yield 20.0 g, 79.4%) as an oily product. This product was used, without further purification, for the subsequent reaction.

Workup

extractionThe product was extracted with ethyl acetate
washThe extract solution was washed with water
customdried
distillationThe solvent was then distilled off

Sources & evidence

ORD record: ord-67fca0d80f674679a540f033bd6de4f6
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034239

Reaction notes

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