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

HRID 1689781Notes

Reaction equation

HRID 1689781 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, about 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is re-dissolved 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 re-dissolved in methanol
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b17a80c024944b0da414944ddb66d728
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

Loading…