Tetrahydrofuran → 1-(3-Ethoxyphenyl)-2-(4-fluorophenyl)-1H-imidazole-4-carboxylic acid

HRID 2356595Notes

Reaction equation

HRID 2356595 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[NH:12])[CH:7]=[CH:8][CH:9]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C([O:32][C:33]1C=C(C=[CH:38][CH:39]=1)N)C.FC1C=CC(C#N)=CC=1.[O:49]1CCCC1>[Cl-].[Na+].O.ClCCl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:38]=[C:39]([C:33]([OH:32])=[O:49])[N:12]=[C:11]2[C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

8

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 121203-EthoxyanilineHCID 145174-FluorobenzonitrileHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178466609HCID 178466609, compound

Product 1

HCID 593841531-(3-Ethoxyphenyl)-2-(4-fluorophenyl)-1H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-(3-Ethoxyphenyl)-4-fluorobenzenecarboximidamide To a solution of 2.2 ml (4.4 mmol) of 2.0 M (in tetrahydrofuran) sodium bis(trimethylsilyl)amide in 5.0 mL of tetrahydrofuran at ambient temperature was added 0.52 mL (4.0 mmol) of 3-ethoxyaniline and the resulting solution was stirred for 20 min. To this reaction mixture was slowly added a solution of 0.48 g (4.0 mmol) of 4-fluorobenzonitrile in 2.0 mL of tetrahydrofuran. The resulting mixture was stirred at ambient temperature for 5 hrs and then poured into brine (25 mL) and dichloromethane (50 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (25 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as yellow solid which was used without further purification. LC/JMS 259.2 (M+1).

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 5 hrs
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (25 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40ff4ad6fc7f46c0a35d88ac7629c940
Source dataset
uspto-grants-2010_07
Patent number
US07759352B2

Reaction notes

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