Lithium Hydroxide → 4-{[(5-Chloro-6-isobutoxypyridin-3-yl)oxy]methyl}-2,5-difluorobenzoic acid

HRID 512034Notes

Reaction equation

HRID 512034 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH2:14][C:15]2[C:24]([F:25])=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17]([F:26])[CH:16]=2)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:12])[CH3:11].[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH2:14][C:15]2[C:24]([F:25])=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([F:26])[CH:16]=2)[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66667691Methyl 4-((5-chloro-6-isobutoxypyridin-3-yloxy)methyl)-2,5-difluorobenzoate

Product 1

HCID 680732444-{[(5-Chloro-6-isobutoxypyridin-3-yl)oxy]methyl}-2,5-difluorobenzoic acidYield 59.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-((5-chloro-6-isobutoxypyridin-3-yloxy)methyl)-2,5-difluorobenzoate (Preparation 4, 623 mg, 1.6 mmol) in THF (10 mL) was added lithium hydroxide (1.8 mL of a 1 M solution in water) and the mixture stirred at room temperature under nitrogen for 18 hours. The solvent was evaporated in vacuo to give the title compound (352 mg, 59%) as a pale yellow solid and was used directly in the next step.

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9c567aa10e3e4255b0cdb12f19087230
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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