Hydrochloric Acid → Methyl 3-bromo-4,7-dimethylindole-2-carboxylate

HRID 361617Notes

Reaction equation

HRID 361617 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[NH:6]2.[Br:16]N1C(=O)CCC1=O.Cl>CN(C=O)C>[Br:16][C:4]1[C:3]2[C:7](=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=2[CH3:1])[NH:6][C:5]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 4714976methyl 4,7-dimethyl-1H-indole-2-carboxylate

Product 1

HCID 53673237Methyl 3-bromo-4,7-dimethylindole-2-carboxylateYield 36.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1.0 g (4.9 mmol) of methyl 4,7-dimethylindole-2-carboxylate in 22 ml of DMF was cooled to 0° C. A solution of 1.03 g (9.8 mmol) of N-bromosuccinimide in 52 ml of DMF was added dropwise at 0° C. over a period of 1 hour and the reaction mixture was stirred for 30 minutes. The reaction mixture was poured into 400 ml of ice water, acidified with a 1N HCl aqueous solution and extracted with 100 ml of ethyl acetate three times. The ethyl acetate layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography to provide 510 mg of yellow crystals. Yield: 36%

Workup

  1. extractionextracted with 100 ml of ethyl acetate three times
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ab50dacf30054c27b861c2e2691a5df2
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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