1H-Indole-5-Carboxylic Acid → methyl 1H-indole-5-carboxylate

HRID 1006106Notes

Reaction equation

HRID 1006106 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:13][Si](C=[N+]=[N-])(C)C>CO.C(Cl)Cl>[CH3:13][O:11][C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)=[O:12]

Participants

4

Reactant 2

HCID 742801H-Indole-5-Carboxylic AcidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 2737635methyl 1H-indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 1H-indole-5-carboxylic acid (5 g, 31.0 mmol) in 70% methanol/methylene chloride (105 mL) at 0° C. was added 1M trimethylsilyldiazomethane in hexanes (46 mL, 46 mmol). After 45 min., the reaction mixture was concentrated to afford 1H-indole-5-carboxylic acid methyl ester (5.2 g).

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-7447bae2acef41a68f0d9da41fda7865
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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