Diethyl Ether → 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-phenylpyrazole

HRID 1274313Notes

Reaction equation

HRID 1274313 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1I.C(=O)([O-])O.[Na+].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCOCC>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 99306665-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-phenylpyrazole

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a rapidly stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (0.25 g) in toluene (2 ml) containing tetrakis(triphenylphosphine)palladium(0) (0.02 g) was added saturated aqueous sodium hydrogen carbonate solution (1 ml) and a solution of phenylboronic acid (0.15 g) in ethanol (1 ml). The mixture was heated under reflux for 1 hour, then left at room temperature overnight and then poured into ether (25 ml) and water (25 ml). The organic layer was separated, dried (MgSO4) and evaporated. The residue was taken up the minimum amount of ethyl acetate and purified by column chromatography on silica gel (20 g) eluted with dichloromethane:hexane (1:1). Combination and evaporation of suitable fractions followed by recrystallisation from ether/hexane gave the title compound as a white solid, m.p. 198-9° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. custompurified by column chromatography on silica gel (20 g)
  7. washeluted with dichloromethane:hexane (1:1)
  8. customCombination and evaporation of suitable fractions
  9. customfollowed by recrystallisation from ether/hexane

Sources & evidence

ORD record
ord-90a7c53c96664034b70102c1f14e1967
Source dataset
uspto-grants-2000_12
Patent number
US06156782

Reaction notes

Loading…