Hydrochloric Acid → 6-(2,6-Difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid

HRID 1499540Notes

Reaction equation

HRID 1499540 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:13][C:12]=1[F:21].[OH-].[Na+].Cl>C1COCC1.CO>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([F:10])[C:3]=1[C:11]1[N:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][C:12]=1[F:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86726771HCID 86726771, compound

Product 1

HCID 592265336-(2,6-Difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acidYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 6-(2,6-difluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (82.9 mg, 0.279 mmol) in THF (0.3 mL) and MeOH (0.3 mL) was added 1.0 M aq. NaOH (1.39 mL, 1.39 mmol). The reaction mixture was stirred at room temperature for 40 min., neutralized with HCl (12 M) to pH=7 and concentrated under reduced pressure to remove the solvents. The residue was dissolved in THF, dried, filtered and concentrated under reduced pressure to give the sub-title compound as a white powder (53.4 mg, 68%). LCMS calc. for C13H9F3NO3 (M+H)+: m/z=284.1. Found: 284.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the solvents
  3. dissolutionThe residue was dissolved in THF
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da3feaf4ebb64fb6aa7e586400bc8119
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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