Trimethylsilyldiazomethane → Methyl 6-Bromo-1H-Indole-3-Carboxylate

HRID 2261759Notes

Reaction equation

HRID 2261759 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:14][Si](C=[N+]=[N-])(C)C>CO>[CH3:14][O:12][C:11]([C:6]1[C:5]2[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1)=[O:13]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 152848376-Bromo-1H-indole-3-carboxylic acid

Product 1

HCID 11499811Methyl 6-Bromo-1H-Indole-3-CarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, approximately 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is redissolved in methanol and concentrated under reduced pressure several times to give the title compound as a solid (100%). ES/MS m/e 256.0 (M+2).

Workup

  1. concentrationThe yellow mixture is concentrated under reduced pressure
  2. dissolutionThe residue is redissolved in methanol
  3. concentrationconcentrated under reduced pressure several times

Sources & evidence

ORD record
ord-e1f15c8edef84905b3ff6b3440d6ca97
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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