Fluorine → HCID 58374107, compound

HRID 1948550Notes

Reaction equation

HRID 1948550 reaction equation
FF.[N+:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[C-:4].[H-].[Na+].[F:13][C:14]([F:25])([F:24])/[C:15](/Cl)=[N:16]/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>C1COCC1>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:16]1[C:15]([C:14]([F:13])([F:24])[F:25])=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[CH:4]1

Participants

6

Reactant 4

HCID 24524FluorineHCID 24758Sodium hydrideHCID 533707Ethyl isocyanoacetateHCID 87214214HCID 87214214, compound

Product 1

HCID 58374107HCID 58374107, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The synthetic intermediate imine (Z)-2,2,2-trifluoro-N-(pyridin-2-yl)acetimidoyl chloride was prepared as described in Huang et al., J. Fluorine Chem., 74:279-282 (1995) and used without distillation. To ethyl isocyanoacetate (0.543 g, 4.8 mmol) in dry THF (50 mL) was added NaH (192 mg, 4 8 mmol, 60% dispersed in oil) at 0° C. and after 5 minutes, (Z)-2,2,2-trifluoro-N-(pyridin-2-yl)acetimidoyl chloride (1.0 g, 4.8 mmol) in 50 mL THF. The reaction mixture was allowed to warm to room temperature and then purified using an 80 g SiO2 column and a 50-100% EtOAc/hexanes gradient. The product eluted to yield 1.23 g (90% yield) of ethyl 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylate as a yellow oil. MS (M+1)=286.1; HPLC RT=1.08 minutes.

Workup

  1. distillation, 74:279-282 (1995) and used without distillation
  2. custompurified
  3. washThe product eluted

Sources & evidence

ORD record
ord-236ae45ce89240169ca0409f9d79ec44
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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