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Cesium carbonate → 4'-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2'-methyl-biphenyl-4-carboxylic acid methyl ester

HRID 424824
Notes
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Reaction equation

HRID 424824 reaction equation
Cl[CH2:2][C:3]1[N:7]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])[N:6]=[N:5][C:4]=1[CH:16]([CH3:18])[CH3:17].[CH3:19][O:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=2[CH3:36])=[CH:25][CH:24]=1)=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:19][O:20][C:21]([C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:2][C:3]3[N:7]([C:8]4[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=4[Cl:15])[N:6]=[N:5][C:4]=3[CH:16]([CH3:18])[CH3:17])=[CH:31][C:30]=2[CH3:36])=[CH:27][CH:28]=1)=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 536647034'-Hydroxy-2'-methyl-biphenyl-4-carboxylic Acid Methyl EsterHCID 667041505-chloromethyl-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-[1,2,3]triazole

Product 1

HCID 667041164'-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2'-methyl-biphenyl-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
55 °C

Procedure

To a solution of 5-chloromethyl-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-[1,2,3]triazole (0.1 g, 0.328 mmol) in dimethylformamide (3 mL) is added 4′-hydroxy-2′methyl-biphenyl-4-carboxylic acid methyl ester (0.079 g, 0.326 mmol) and cesium carbonate (0.21 g, 0.646 mmol). The reaction is heated to 55° C. for 2.5 h and is cooled to room temperature. The reaction mixture is concentrated under reduced pressure. The residue is dissolved in 1N hydrochloric acid and ethyl acetate. The layers are separated and the aqueous is extracted again with ethyl acetate. The organic layers are combined and are washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 4′-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2′-methyl-biphenyl-4-carboxylic acid methyl ester. ES/MS m/e (35Cl/37Cl) 510.2/512.2 (M+1).

Workup

  1. temperatureis cooled to room temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in 1N hydrochloric acid
  4. customThe layers are separated
  5. extractionthe aqueous is extracted again with ethyl acetate
  6. washare washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c65f2a1aa3f54769b0fdea1e7d588d1e
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106077B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes