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

HRID 250229Notes

Reaction equation

HRID 250229 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>[CH3:15][O:13][C:12](=[O:14])[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 967345-Bromo-3-indoleacetic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 49782545methyl 2-(5-bromo-1H-indol-3-yl)acetateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (5-bromo-1H-indol-3-yl)-acetic acid (683 mg, 2.69 mmol) in methanol (6 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, approximately 6 mL) over two minutes at room temperature. The yellow mixture is concentrated. The residue is taken up in methanol and is concentrated several times to give of the title compound (710 mg, 99%). ES/MS m/e 266.2 (M−2).

Workup

  1. concentrationThe yellow mixture is concentrated
  2. concentrationis concentrated several times

Sources & evidence

ORD record
ord-ae807f98bc08481ba5fe2c9bb370e741
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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