Hydrochloric Acid → 5-(2,2-Difluoroethoxy)-3-fluoro-pyridine-2-carboxylic acid

HRID 1754866Notes

Reaction equation

HRID 1754866 reaction equation
[OH-].[Na+].[F:3][CH:4]([F:19])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([F:18])[C:10]([C:13]([O:15]CC)=[O:14])=[N:11][CH:12]=1.Cl.O1CCOCC1>C1COCC1>[F:19][CH:4]([F:3])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([F:18])[C:10]([C:13]([OH:15])=[O:14])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 117738010Ethyl 5-(2,2-difluoroethoxy)-3-fluoro-pyridine-2-carboxylate

Product 1

HCID 1177387615-(2,2-Difluoroethoxy)-3-fluoro-pyridine-2-carboxylic acidYield 229.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (2 M in water, 2.43 mL, 4.86 mmol) is added to a solution of ethyl 5-(2,2-difluoroethoxy)-3-fluoro-pyridine-2-carboxylate (242 mg, 0.97 mmol) in THF (10 mL). The reaction is stirred at room temperature for 5 days. The reaction is quenched by the addition of 4 M HCl in dioxane (1.25 mL, 5 mmol) and the solution is concentrated to give the crude title compound (493 mg, 229%). ES/MS (m/e): 222.0 (M+1).

Workup

  1. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-002f680a6c324eebadb6866fa0181829
Source dataset
uspto-grants-2015_10
Patent number
US09169271B2

Reaction notes

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