Pyridine → 1-(3-chlorophenyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester

HRID 334008Notes

Reaction equation

HRID 334008 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.[NH:11]1[CH:15]=[N:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[N:12]1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:19][O:18][C:16]([C:13]1[N:14]=[CH:15][N:11]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:12]=1)=[O:17]

Participants

6

Reactant 3

HCID 1049PyridineHCID 2734323(3-Chlorophenyl)boronic acidHCID 178499122HCID 178499122, compound

Product 1

HCID 694601791-(3-chlorophenyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 12.1 g (77.1 mmol) 3-chlorophenylboronic acid and 10.0 g (77.1 mmol) methyl 1,2,4-triazole-3-carboxylate in 200 mL DCM was added 19.0 mL (235 mmol) pyridine followed by 14.0 g (77.1 mmol) copper (II) acetate. The reaction mixture was stirred at RT for 3 days, and then filtered over celite. The filtrate was washed with 1M aqueous KHSO4 solution and saturated aqueous bicarbonate solution. The organic layer was dried over sodium sulfate, concentrated in vacuo and dried.

Workup

  1. filtrationfiltered over celite
  2. washThe filtrate was washed with 1M aqueous KHSO4 solution and saturated aqueous bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customdried

Sources & evidence

ORD record
ord-8ee34a94e7244845a4ffc8244b75ae50
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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