1-(3-chloro-2-methoxyphenyl)-5-iodo-3-(trifluoromethyl)-1H-pyrazole → 1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile

HRID 1842891Notes

Reaction equation

HRID 1842891 reaction equation
[Cl:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([N:8]2[C:12](I)=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:20]([Cu])#[N:21]>CN1C(=O)CCC1>[Cl:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([N:8]2[C:12]([C:20]#[N:21])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 708161331-(3-chloro-2-methoxyphenyl)-5-iodo-3-(trifluoromethyl)-1H-pyrazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 708164511-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrileYield 33.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a stirred solution of 1-(3-chloro-2-methoxyphenyl)-5-iodo-3-(trifluoromethyl)-1H-pyrazole (0.2 g, 0.49 mmol, 1.0 eq) in NMP (5 mL) was added CuCN (0.044 g, 0.49 mmol, 1.0 eq) and heated to 200° C. for 2 h. The reaction mixture was passed through celite pad and washed with excess of ethyl acetate. The filtrate was washed with water and ethyl acetate layer was separated, dried (Na2SO4), and the solvent evaporated. The resulting residue was purified by CC using ethyl acetate/PE (1:19) to get 1-(3-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile (0.05 g, crude, yellow solid; TLC system: EtOAc/PE (1:9) Rf: 0.5).

Workup

  1. washwashed with excess of ethyl acetate
  2. washThe filtrate was washed with water and ethyl acetate layer
  3. customwas separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated
  6. customThe resulting residue was purified by CC

Sources & evidence

ORD record
ord-ea0c224130bd40d68a3e722f59804d94
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

Loading…