Chlorotrimethylsilane → HCID 58843127, compound

HRID 384861Notes

Reaction equation

HRID 384861 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][C:13]([OH:15])=[O:14].[CH3:16][Si](Cl)(C)C>CO>[CH3:16][O:14][C:13](=[O:15])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 184500383-(5-Bromo-1H-indol-3-yl)propanoic acid

Product 1

HCID 58843127HCID 58843127, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 5-bromoindole-3-propionic acid 87 (4.0 g, 14.91 mmol) was dissolved in methanol (MeOH, 100 mL) and Trimethylsilyl chloride (TMSCl, 33.0 mL, 32.8 mmol, 1.0 M in CH2Cl2) was added dropwise The mixture was stirred for 24 hours, followed by refluxing for 1 hour. The reaction was allowed to cool to room temperature and the solvent was evaporated to ester as a white solid, (M+1=284).

Workup

  1. temperatureby refluxing for 1 hour
  2. customthe solvent was evaporated to ester as a white solid, (M+1=284)

Sources & evidence

ORD record
ord-55f1478b13a146fdbfbde1ae7ca4cf7d
Source dataset
uspto-grants-2013_02
Patent number
US08367828B2

Reaction notes

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