Water → 3-(4-Fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylic acid

HRID 1251923Notes

Reaction equation

HRID 1251923 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][CH2:7][C:8]2[C:9]([C:30]([O:32]C)=[O:31])=[N:10][C:11]([O:14][CH:15]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:16][C:17]3[N:21]([CH3:22])[CH:20]=[N:19][CH:18]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O>CO>[F:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][CH2:7][C:8]2[C:9]([C:30]([OH:32])=[O:31])=[N:10][C:11]([O:14][CH:15]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:16][C:17]3[N:21]([CH3:22])[CH:20]=[N:19][CH:18]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18324461Methyl 3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylate

Product 1

HCID 183243783-(4-Fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylic acidYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylate (1.56 g), sodium hydroxide (0.65 g), water (12 ml) and methanol (80 ml) was heated at reflux for 16 hours and then cooled to ambient temperature. The mixture was concentrated under reduced pressure, 1M citric acid (17 ml) added and the mixture extracted with 10% methanol/dichloromethane (1×50 ml, 2×30 ml). The extracts were dried and concentrated under reduced pressure to give 3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylic acid as a pale yellow foam (1.22 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. concentrationThe mixture was concentrated under reduced pressure, 1M citric acid (17 ml)
  4. additionadded
  5. extractionthe mixture extracted with 10% methanol/dichloromethane (1×50 ml, 2×30 ml)
  6. customThe extracts were dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b242954fa7044c409f4f0a30a0fa1f35
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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