Hydrogen Peroxide → 2-(6-bromo-1H-indol-3-yl)acetamide

HRID 2215748Notes

Reaction equation

HRID 2215748 reaction equation
C([O-])([O-])=[O:2].[K+].[K+].[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH2:17][C:18]#[N:19])=[CH:13][NH:14]2)=[CH:10][CH:9]=1.O.OO>CS(C)=O>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([CH2:17][C:18]([NH2:19])=[O:2])=[CH:13][NH:14]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 158193282-(6-bromo-1H-indol-3-yl)acetonitrile

Product 1

HCID 234276092-(6-bromo-1H-indol-3-yl)acetamideYield 58.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Powdered K2CO3 (408 mg, 2.95 mmol, 1.60 eq.) was heated to 50° C. in DMSO (3 mL) for 20 min, then cooled to rt. 6-Bromo-1H-indole-3-acetonitrile (434 mg, 1.85 mmol) was dissolved in DMSO (3 mL) and added to the reaction slurry. Water (0.2 mL) and aqueous 30% H2O2 (0.46 mL, 4.0 mmol, 2.2 eq.) were added, and the reaction mixture was stirred for 2–3 hours at rt. The reaction was quenched with 1N HCl and extracted with EtOAc. The organic layer was washed with 1.5 N sodium thiosulfate and dried (MgSO4). The solvent was removed in vacuo, and the residue crystallized from CH2Cl2 to give 273 mg (55%) of the title compound.

Workup

  1. additionadded to the reaction slurry
  2. customThe reaction was quenched with 1N HCl
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with 1.5 N sodium thiosulfate
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue crystallized from CH2Cl2

Sources & evidence

ORD record
ord-b7e94b8d117b4f27a187e31998ea634a
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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