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

HRID 60909

Reaction equation

HRID 60909 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:12]1[CH:16]=[CH:15][N:14]=[N:13]1.CN[C@H]1CCCC[C@@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]([N:13]2[N:14]=[CH:15][CH:16]=[N:12]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2280802-Bromo-5-methylbenzoic acidHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 178418936HCID 178418936, compound

Product 1

HCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acidYield 79.4%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromo-5-methylbenzoic acid (2.0 g, 9.30 mmol), 1,2,3-triazole (1.08 mL, 18.6 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (2.23 mL, 13.95 mmol), Cs2CO3 (4.55 g, 13.95 mmol) and CuI (124 mg, 0.65 mmol) in DMF (12 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The reaction was cooled to rt, diluted with MeOH, and acidified with AcOH to pH 4-5. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% DCM/EtOAc) to yield the title compound as a yellow oil (1.5 g, 61%). MS (ESI) 204 (M+H).

Workup

  1. customwas degassed
  2. temperatureThe reaction was cooled to rt
  3. additiondiluted with MeOH
  4. customThe solvent was removed in vacuo
  5. customto obtain the crude which
  6. customwas purified by silica gel chromatography (0˜100% DCM/EtOAc)

Sources & evidence

ORD record
ord-f9bf1d451c994de585039736b601cfed
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Linked notes

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