Acetic Acid → Methyl [4-bromo-2-methyl-5-(methyloxy)-1h-indol-3-yl]acetate

HRID 12624Notes

Reaction equation

HRID 12624 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]([O:20][CH3:21])=[CH:10][CH:9]=2.[Br:22]Br.C(=O)([O-])O.[Na+]>O>[Br:22][C:12]1[C:11]([O:20][CH3:21])=[CH:10][CH:9]=[C:8]2[C:13]=1[C:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:6]([CH3:5])[NH:7]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 82067methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetateHCID 516892Sodium Bicarbonate

Product 1

HCID 91304785Methyl [4-bromo-2-methyl-5-(methyloxy)-1h-indol-3-yl]acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an acetic acid (12 mL) solution of methyl [2-methyl-5-(methyloxy)-1H-indol-3-yl]acetate (300 mg), bromine (206 mg) was added and the mixture was stirred at room temperature for one hour. To the reaction mixture, water and an aqueous saturated sodium hydrogen carbonate solution were added, followed by extraction with ethyl acetate. The organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=65:35→60:40) to obtain the titled compound having the following physical properties (134 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed in turn with an aqueous saturated sodium hydrogen carbonate solution, water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=65:35→60:40)

Sources & evidence

ORD record
ord-2d289fed0e074cd691f580ff0c9eda52
Source dataset
uspto-grants-2010_06
Patent number
US07728023B2

Reaction notes

Loading…