3-Ethynylpyridine → 3,4-Dimethyl-5-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-benzoic acid

HRID 1350655Notes

Reaction equation

HRID 1350655 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([CH3:14])[C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])=[N+:2]=[N-:3].[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)#[CH:16]>CCO>[CH3:14][C:11]1[CH:10]=[C:6]([CH:5]=[C:4]([N:1]2[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[N:3]=[N:2]2)[C:12]=1[CH3:13])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 1860033-EthynylpyridineHCID 179731283-Azido-4,5-dimethyl benzoic acid

Product 1

HCID 210972963,4-Dimethyl-5-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-benzoic acidYield 32.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of 100 mg (0.52 mmol) of 3-azido-4,5-dimethyl benzoic acid (U.S. Ser. No. 04/102,492), 54 mg (0.52 mmol) of 3-ethynyl pyridine, and 200 μL of EtOH was heated to 120° C. in a sealed tube for 12 h. The mixture was cooled and diluted with 500 μL of EtOH. The mixture was filtered and the solids were washed with EtOH (3×0.5 mL). The solids were dried to provide 50 mg of 3,4-dimethyl-5-(4-pyridin-3-yl-[1,2,3]triazol-1-yl)-benzoic acid.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe mixture was filtered
  3. washthe solids were washed with EtOH (3×0.5 mL)
  4. customThe solids were dried

Sources & evidence

ORD record
ord-9203aa5901604990b90505741f92cca8
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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