Azidotrimethylsilane → 2-Chloro-5-(2H-[1,2,3]triazol-4-yl)-benzoic acid methyl ester

HRID 456884Notes

Reaction equation

HRID 456884 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:10]#[CH:11])[CH:7]=[CH:6][C:5]=1[Cl:12].C[Si]([N:18]=[N+:19]=[N-:20])(C)C>C(O)CCC>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:20][NH:19][N:18]=2)[CH:7]=[CH:6][C:5]=1[Cl:12]

Participants

4

Reactant 2

HCID 78378Azidotrimethylsilane3×HCID 86595910Methyl 2-chloro-5-ethynylbenzoate

Product 1

HCID 588181912-Chloro-5-(2H-[1,2,3]triazol-4-yl)-benzoic acid methyl esterYield 43.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-chloro-5-ethynyl-benzoic acid methyl ester (0.18 g, 0.92 mmol) and trimethylsilyl azide (0.16 g, 1.39 mmol) in n-butanol was heated to reflux for 16 h. A second portion of trimethylsilyl azide (0.16 g, 1.39 mmol) was added and the mixture was refluxed for a further 16 h. A third portion of trimethylsilyl azide (0.16 g, 1.39 mmol) was added and the mixture was refluxed for a further 16 h. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by flash column chromatography (2:1 hexanes-ethyl acetate) to afford the title compound (0.095 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. temperaturethe mixture was refluxed for a further 16 h
  4. temperaturethe mixture was refluxed for a further 16 h
  5. additionSilica gel was added
  6. concentrationthe mixture was concentrated in vacuo
  7. customThe residue was purified by flash column chromatography (2:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-8d012f47c149417296b02fe9b3c78619
Source dataset
uspto-grants-2007_03
Patent number
US07186742B2

Reaction notes

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