Cesium carbonate → 5-chloro-4-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 1477741Notes

Reaction equation

HRID 1477741 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].C[O:8][C:9](=[O:19])[C:10]1[CH:15]=[C:14]([Cl:16])[C:13]([CH3:17])=[CH:12][C:11]=1Br.[NH:20]1[CH:24]=[CH:23][N:22]=[N:21]1>CN(C=O)C>[Cl:16][C:14]1[C:13]([CH3:17])=[CH:12][C:11]([N:21]2[N:22]=[CH:23][CH:24]=[N:20]2)=[C:10]([CH:15]=1)[C:9]([OH:8])=[O:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 533306162-Bromo-5-chloro-4-methyl-benzoic acid methyl esterHCID 178418936HCID 178418936, compound

Product 1

HCID 895599375-chloro-4-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Cs2CO3 (742 mg, 2.28 mmol) was added portionwise to a rt solution of 2-bromo-5-chloro-4-methyl-benzoic acid methyl ester (300 mg, 1.14 mmol) in DMF (3 mL) followed by 1H-1,2,3-triazole (0.1 mL, 1.71 mmol), Cu(I)I (13 mg, 0.068 mmol) and DMCDA (40 uL, 0.23 mmol). The resulting suspension was stirred at 120° C. for 4 h. The rxn mixture was quenched with 2M aq. HCl and extracted with EtOAc (3×). The combined org. layers were dried (Na2SO4), filtered and evaporated in vacuo to obtain the crude product that was purified by prep. HPLC (method C) to give the title compound A-1-15 as a pale yellow solid. LC-MS A: tR=0.72 min; [M(35Cl)+H]+=238.01.

Workup

  1. customThe rxn mixture was quenched with 2M aq. HCl
  2. extractionextracted with EtOAc (3×)
  3. dry with materiallayers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto obtain the crude product that
  7. customwas purified by prep

Sources & evidence

ORD record
ord-cea47823113e429f9b69370281203292
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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