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

HRID 1760782Notes

Reaction equation

HRID 1760782 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 5-indole carboxylic acid (5.08 g, 31.5 mmol) in a 1:1 mixture of methanol/methylene chloride (40 mL) was added (trimethylsilyl)diazomethane (33 mL, 2 M solution in hexanes) in portions over 15 min. The yellow colored solution was concentrated on the rotoevaporator to provide methyl-5-indole carboxylate as a white powder (5.5 g).

Workup

  1. concentrationThe yellow colored solution was concentrated on the rotoevaporator

Sources & evidence

ORD record
ord-0498a502e31943c287ae2b66926dd362
Source dataset
uspto-grants-2005_01
Patent number
US06844366B2

Reaction notes

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