Lithium Hydroxide → 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetic acid

HRID 1799147Notes

Reaction equation

HRID 1799147 reaction equation
[OH-].[Li+].[Br:3][C:4]1[N:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=2)[C:7]([S:21][C:22]([F:29])([F:28])[C:23]([O:25]CC)=[O:24])=[N:6][CH:5]=1>C1COCC1.C(O)C.O>[Br:3][C:4]1[N:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=2)[C:7]([S:21][C:22]([F:29])([F:28])[C:23]([OH:25])=[O:24])=[N:6][CH:5]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59225861ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate

Product 1

HCID 592258722-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetic acid

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous lithium hydroxide solution (1M, 2 eq) was added to a solution of ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetate (1 eq) in THF, ethanol and water, and stirred for 4 h. After concentrating, the residue was acidified with aqueous HCl solution (1N), diluted with water and filtered to afford 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)-2,2-difluoroacetic acid.

Workup

  1. concentrationAfter concentrating
  2. additiondiluted with water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ab4fb307e814476fb15ee20202fe69bd
Source dataset
uspto-grants-2013_01
Patent number
US08344012B2

Reaction notes

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