5-Bromo-3-indoleacetic acid → methyl 2-(5-bromo-1H-indol-3-yl)acetate

HRID 1819683Notes

Reaction equation

HRID 1819683 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([OH:14])=[O:13].[CH3:15][Si](C=[N+]=[N-])(C)C>CO.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 967345-Bromo-3-indoleacetic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 49782545methyl 2-(5-bromo-1H-indol-3-yl)acetateYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Step H (1): To a solution of 2-(5-bromo-1H-indol-3-yl)acetic acid (1.0 g 3.94 mmol) in MeOH (5 mL) and Et2O (15 mL) was added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, 10 mL). The reaction was stirred at rt for 2 h. The solvents were removed and the residue was purified by flash chromatography to yield 900 mg of methyl 2-(5-bromo-1H-indol-3-yl)acetate (yield 85%). 1H NMR (500 MHz, CDCl3) δ ppm 3.71 (s, 3 H) 3.72 (s, 2 H) 7.16 (d, J=2.14 Hz, 1 H) 7.21 (d, J=8.55 Hz, 1 H) 7.27 (dd, J=8.55, 1.83 Hz, 1 H) 7.72 (d, J=1.53 Hz, 1 H) 8.12 (s, 1 H)

Workup

  1. customThe solvents were removed
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7da81e6cf6994cf7bc41a092ccd24e9e
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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