Trimethylsilyldiazomethane → Methyl[6-chloro-2-(1-methylimidazole-2-carbonyl)-1h-indol-3-yl]acetate

HRID 396546Notes

Reaction equation

HRID 396546 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:19][C:20]([OH:22])=[O:21])=[C:7]([C:11]([C:13]3[N:14]([CH3:18])[CH:15]=[CH:16][N:17]=3)=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[CH3:23][Si](C=[N+]=[N-])(C)C>CO>[CH3:23][O:21][C:20](=[O:22])[CH2:19][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][C:7]=1[C:11]([C:13]1[N:14]([CH3:18])[CH:15]=[CH:16][N:17]=1)=[O:12]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 18542187[6-Chloro-2-(1-methylimidazole-2-carbonyl)-1H-indol-3-yl]acetic Acid

Product 1

HCID 23003281Methyl[6-chloro-2-(1-methylimidazole-2-carbonyl)-1h-indol-3-yl]acetateYield 28.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of [6-chloro-2-(1-methylimidazole-2-carbonyl)indol-3-yl]acetic acid (Example 241, 65 mg, 0.21 mmol) in methanol (10 ml) was added (trimethylsilyl)diazomethane (1.0 M solution in hexanes, 1.05 ml, 2.1 mmol) at room temperature. After stirring for 19 h, the mixture was concentrated. The residue was purified by TLC developing with ethyl acetate-hexane (1:2) to afford 20 mg (23%) of the title compound as yellow solids.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by TLC

Sources & evidence

ORD record
ord-70d415c36f344e9e99017a3ab5d7a5c6
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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