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Water → ethyl 2-ethoxy-3-(4-{2-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]ethoxy}phenyl)propanoate

HRID 273358
Notes
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Reaction equation

HRID 273358 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([O:18][CH2:19][CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[F:27][C:28]([F:39])([F:38])[C:29]1[NH:30][C:31]2[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=2[N:33]=1.O>CN(C=O)C>[CH2:19]([O:18][CH:12]([CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:30]2[C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[N:33]=[C:29]2[C:28]([F:27])([F:39])[F:38])=[CH:6][CH:7]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 675602-(Trifluoromethyl)-1H-benzimidazoleHCID 11002461Ethyl 2-ethoxy-3-[4-(2-bromoethoxy)-phenyl]propanoate

Product 1

HCID 11851905ethyl 2-ethoxy-3-(4-{2-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]ethoxy}phenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

Ethyl 3-[4-(2-bromoethoxy)phenyl]-2-ethoxypropanoate (371 mg, 1 mmol) was dissolved in DMF (5 ml) and K2CO3 (552 mg, 4 mmol) was added followed by 2-trifluoromethyl benzimidazole (204 mg, 1.1 mmol). The reaction mixture was heated to 60° C. for 17 hrs. After the completion of the reaction, water was added and the product was extracted with Et2O. The product was purified by column chromatography on silica gel using ethyl acetate and hexanes as solvent (333 mg, 70%).

Workup

  1. additionwas added
  2. extractionthe product was extracted with Et2O
  3. customThe product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5c1f524d6c164b598590e111d35718df
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07456293B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes