HCID 70816986, compound → HCID 70816662, compound

HRID 1842895Notes

Reaction equation

HRID 1842895 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([N:8]2[C:12](I)=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)[CH:7]=1.[C:20]([Cu])#[N:21]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([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:7]=1

Participants

4

Reactant 2

HCID 70816986HCID 70816986, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 70816662HCID 70816662, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a stirred solution of 1-(5-chloro-2-methoxyphenyl)-5-iodo-3-(trifluoromethyl)-1H-pyrazole (4.83 g, 12.01 mmol, 1.0 eq) in NMP (20 mL) was added CuCN (1.03 g, 12.01 mmol, 1.0 eq) and the mixture heated to 200° C. for 2 h. The reaction mixture was passed through a celite pad and washed with excess of ethyl acetate. The filtrate was washed with water and the 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-(5-chloro-2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile (3.85 g, crude, yellow solid; TLC system: EtOAc/PE (1:4) Rf: 0.65).

Workup

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

Sources & evidence

ORD record
ord-55db2433d540456289a7e801ee40a0c2
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

Loading…