Water → 2-(5-chloro-1H-indol-1-yl)propanamide

HRID 2424335Notes

Reaction equation

HRID 2424335 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.Br[CH:14]([CH3:18])[C:15]([NH2:17])=[O:16].O>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:14]([CH3:18])[C:15]([NH2:17])=[O:16])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 871105-ChloroindoleHCID 1011182-Bromopropanamide

Product 1

HCID 591297552-(5-chloro-1H-indol-1-yl)propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A dispersion of 60% NaH (6.85 g, 0.17 mol) was added to an ice-cooled solution of 5-chloroindole (20 g, 0.13 mol) in 250 ml of dry DMF. The stirring was continued for 20 minutes at room temperature, and the mixture was cooled again with an ice bath. After portionwise addition of solid 2-bromopropanamide (24.1 g, 0.15 mol), the reaction mixture was stirred for 1 h30 at room temperature, then poured into cold water and extracted 3 times with AcOEt. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (AcOEt/hexane 50/50) to give pure 2-(5-chloro-1H-indol-1-yl)propanamide 25 as a white solid.

Workup

  1. temperaturethe mixture was cooled again with an ice bath
  2. extractionextracted 3 times with AcOEt
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel chromatography (AcOEt/hexane 50/50)

Sources & evidence

ORD record
ord-b97f15a947b449f5b3948a381f506a48
Source dataset
uspto-grants-2011_06
Patent number
US07964593B2

Reaction notes

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