Methanol → Methyl 4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]-benzoate

HRID 479755Notes

Reaction equation

HRID 479755 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Na].[OH-].[Na+].[CH3:31]O>Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([O:25][CH3:31])=[O:24])=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 110574684-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzoic acid

Product 1

HCID 10133915Methyl 4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]-benzoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

A mixture containing 4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzoic acid, sodium salt (0.20 g, 0.5 mmol) [See Ex. 9 above] and concentrated HCl (10 drops) in MeOH (5 mL) was heated at reflux for 8 h. After cooling, the pH was adjusted to neutral by the addition of 2.5 N NaOH, and the solid which formed was collected by filtration, washed with H2O and dried in vacuo. The title compound was obtained as a yellow solid (0.14 g, 76%) and was recrystallized from EtOAc/CH2Cl2; 1H NMR (CDCl3/MeOH-d4); d 8.36 (d, 2H); 8.03 (m, 4H); 7.60 -7.30 (m, 4H); 7.07 (t, 2H); 3.84 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. temperatureAfter cooling
  4. customthe solid which formed
  5. filtrationwas collected by filtration
  6. washwashed with H2O
  7. customdried in vacuo

Sources & evidence

ORD record
ord-bb02f26815274bd2bbb59a9d1c40a307
Source dataset
uspto-grants-2003_11
Patent number
US06645989B2

Reaction notes

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