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

HRID 1371906Notes

Reaction equation

HRID 1371906 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([OH:3])=[O:2].[Si](C=[N+]=[N-])(C)(C)[CH3:14]>ClCCl.CO>[CH3:14][O:2][C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)=[O:3]

Participants

5

Reactant 2

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

Product 1

HCID 2737635methyl 1H-indole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Combine 5-carboxyindole (7.2 g, 44.7 mmol) in 400 mL dichloromethane and 100 mL MeOH and treat dropwise with 35 mL 2 M TMS diazomethane in hexanes. Stir overnight at ambient temperature. Concentration under vacuum to give the title compound as a solid: Analysis for C10H9NO2 0.1H2O: calcd: C, 67.86; H, 5.24; N, 7.91; found: C, 68.03; H, 5.15; N, 7.98; 1H NMR (CDCl3) 8.44 (bs, 1H), 8.412–8.409 (m, 1H), 7.91–7.88 (m, 1H), 7.46–7.38 (m, 1H), 7.26–7.24 (m, 1H), 6.64–6.63 (m, 1H), 3.92 (s, 3H); ISMS 176 (M+1).

Workup

  1. concentrationConcentration under vacuum

Sources & evidence

ORD record
ord-6b486d0b68d84ab38543425d4137da2e
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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