Trifluoroacetic acid → 4-(2-Fluorophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid

HRID 454759Notes

Reaction equation

HRID 454759 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:27]=[CH:26][C:18]([C:19]([O:21]C(C)(C)C)=[O:20])=[C:17]([NH:28][C:29]([C:31]2[CH:32]=[N:33][CH:34]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:36]=2)=[O:30])[CH:16]=1>>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:27]=[CH:26][C:18]([C:19]([OH:21])=[O:20])=[C:17]([NH:28][C:29]([C:31]2[CH:32]=[N:33][CH:34]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:36]=2)=[O:30])[CH:16]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508706Tert-butyl 4-(2-fluorophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate

Product 1

HCID 585085154-(2-Fluorophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid

Procedure

Trifluoroacetic acid (3.0 mL) was added to the obtained tert-butyl 4-(2-fluorophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate, followed by stirring at room temperature for 1 hour and 30 minutes. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration. Dioxane (3.0 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.041 mL) were added to the obtained solid substance, followed by stirring at room temperature for 1 hour. A 10% aqueous solution of citric acid was added to the reaction mixture, and the solid substance was collected by filtration to obtain 36 mg of 4-(2-fluorophenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  2. additionwas added to the obtained residue
  3. filtrationThe solid substance was collected by filtration
  4. additionDioxane (3.0 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.041 mL) were added to the obtained solid substance
  5. stirringby stirring at room temperature for 1 hour
  6. additionA 10% aqueous solution of citric acid was added to the reaction mixture
  7. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-fd64c3afc8fa4d918ef78f2dde168b2e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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