Cesium carbonate → 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 1750465Notes

Reaction equation

HRID 1750465 reaction equation
[N:1]1[NH:2][N:3]=[CH:4][CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN[C@@H]1CCCC[C@H]1NC.I[C:23]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:24]=1[C:25]([OH:27])=[O:26]>CN(C=O)C.[Cu]I.O>[CH3:32][C:29]1[CH:30]=[CH:31][C:23]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 675161H-1,2,3-TriazoleHCID 1429412-Iodo-5-methylbenzoic acidHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

Product 1

HCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2H-1,2,3-triazole (CAS number 288-36-8; 1.99 g, 28.93 mmol) in DMF (7.0 ml) at 0-10° C. was added cesium carbonate (4.7 g, 14.45 mmol), trans-1-N,2-N-dimethylcyclohexane-1,2-diamine (0.127 g, 1.45 mmol), copper(I) iodide (0.068 g, 0.36 mmol) and 2-iodo-5-methylbenzoic acid (CAS number 52548-14-8; 3.79 g, 14.46 mmol). The reaction was subjected to microwave irradiation at 125° C. for 15 minutes, and then poured into water (20 ml) and extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (0-3% methanol/DCM) to afford the title compound.

Workup

  1. customirradiation at 125° C. for 15 minutes
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography (0-3% methanol/DCM)

Sources & evidence

ORD record
ord-f8980bc175254265a800d618993df220
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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