Trimethylsilyldiazomethane → methyl 6-hydroxy-1H-indole-2-carboxylate

HRID 1874880Notes

Reaction equation

HRID 1874880 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[OH:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([OH:20])=[O:19])[NH:15]2)=[CH:11][CH:10]=1>CO>[OH:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([O:20][CH3:1])=[O:19])[NH:15]2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 223501916-Hydroxy-1H-indole-2-carboxylic acid

Product 1

HCID 10535709methyl 6-hydroxy-1H-indole-2-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2M solution of trimethylsilyldiazomethane in hexanes was added to a solution of 6-hydroxy-1H-indole-2-carboxylic acid (0.500 g, 2.82 mmol) in MeOH until the solution remained yellow in color. The solution was stirred at RT until the starting material was consumed as evident by TLC. The reaction mixture was partitioned between water and EtOAc then the organic layer was separated, dried over MgSO4, filtered and concentrated. Purification was accomplished by column chromatography (EtOAc/hexanes) to afford the title compound (0.464 g, 86% yield). 1H NMR (400 MHz, Acetone-d6): δ ppm 10.55 (br. s., 1H), 8.32 (s, 1H), 7.50 (d, 1H), 7.09 (d, 1H), 6.95 (d, 1H), 6.74 (dd, 1H), 3.85 (s, 3H). MS m/z=191.9 (M+1).

Workup

  1. customwas consumed as evident by TLC
  2. customThe reaction mixture was partitioned between water and EtOAc
  3. customthe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification

Sources & evidence

ORD record
ord-8b4e91699266435dabd449cde3668a6f
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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