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

HRID 1747221Notes

Reaction equation

HRID 1747221 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 μL, 0.23 mmol). The resulting suspension was heated to 120° C. for 4 h. The reaction mixture was cooled to RT, quenched with 2M aq. HCl and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and evaporated in vacuo to give the crude product that was purified by prep. HPLC (method E) to give the title compound as a pale yellow solid. LC-MS A: tR=0.72 min; [M(35Cl)+H]+=238.01.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customquenched with 2M aq. HCl
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give the crude product that
  8. customwas purified by prep

Sources & evidence

ORD record
ord-950c18dcc49643299979d46840781bea
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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