Diethyl Ether → 5-Difluoromethympyrazine-2-carboxylic acid

HRID 2281842Notes

Reaction equation

HRID 2281842 reaction equation
FC(F)(F)C(O)=O.[F:8][CH:9]([F:23])[C:10]1[N:11]=[CH:12][C:13]([C:16]([O:18]C(C)(C)C)=[O:17])=[N:14][CH:15]=1.CCOCC.[OH-].[Na+]>ClCCl>[F:23][CH:9]([F:8])[C:10]1[N:11]=[CH:12][C:13]([C:16]([OH:18])=[O:17])=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 57475685t-Butyl 5-difluoromethylpyrazine-2-carboxylate

Product 1

HCID 574685755-Difluoromethympyrazine-2-carboxylic acidYield 75.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to a solution of t-butyl 5-difluoromethylpyrazine-2-carboxylate (175 mg) in dichloromethane (1 mL), and the mixture was stirred at RT for 5 h. Ether and 5 N NaOH were added to the reaction solution. The aqueous layer was separated and made acidic with 5 N hydrochloric acid. EtOAc was added to the aqueous layer, and the organic layer was separated. The organic layer was dried over anhydrous MgSO4, and the insoluble matter was separated by filtration. The filtrate was concentrated to obtain the title compound (100 mg). 1H-NMR (CDCl3) δ (ppm): 6.80 (t, J=54.4 Hz, 1H), 9.02 (s, 1H), 9.47 (s, 1H).

Workup

  1. customThe aqueous layer was separated
  2. additionEtOAc was added to the aqueous layer
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. customthe insoluble matter was separated by filtration
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1cb70db88fb64ac78b906ff7a4248d3a
Source dataset
uspto-grants-2015_09
Patent number
US09139594B2

Reaction notes

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