Trimethylsilylmethyl Azide → 5-Pyridin-2-yl-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

HRID 402373

Reaction equation

HRID 402373 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]#[C:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH3:2].[N:14]([CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[N+:15]=[N-:16]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[N:14]([CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:15]=[N:16][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 150751Trimethylsilylmethyl AzideHCID 12426870Ethyl 3-(pyridin-2-yl)prop-2-ynoate

Product 1

HCID 674985495-Pyridin-2-yl-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl esterYield 23%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of pyridin-2-yl-propynoic acid ethyl ester (1.25 g, 7.14 mmol) in benzene (22 mL) was added azidomethyl-trimethyl-silane (1.11 g, 8.56 mmol) and the reaction mixture was refluxed under nitrogen for 72 h. The mixture was then evaporated and purification by chromatography [silica, 0 to 50% ethyl acetate in heptane then HPLC (Chiralpak AD, ethanol in heptane)] afforded the title compound (477 mg, 23%) as a yellow oil. MS: m/e=305.2 [M+H]+.

Workup

  1. temperaturethe reaction mixture was refluxed under nitrogen for 72 h
  2. customThe mixture was then evaporated
  3. custompurification by chromatography [silica, 0 to 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-4c3e19444d9640c290840605db9e15fc
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Linked notes

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