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

HRID 424784Notes

Reaction equation

HRID 424784 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, ca 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. This process is repeated 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

Sources & evidence

ORD record
ord-ac25de849d0d4fa59b9d1e1470248bb4
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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