Diethyl Ether → HCID 22120913, compound

HRID 1108802Notes

Reaction equation

HRID 1108802 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+].[NH2:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=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:32]1[CH:31]=[CH:30][CH:29]=[C:28]([NH2:27])[CH:33]=1

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 922693-Aminophenylboronic acidHCID 516892Sodium Bicarbonate2×HCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 22120913HCID 22120913, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a rapidly stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (0.447 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 3-aminophenylboronic acid (0.310 g) in ethanol (1 ml). The mixture was heated under reflux for 3 hours, then left at room temperature overnight. Saturated aqueous sodium hydrogen carbonate solution (0.5 ml) and tetrakis(triphenylphosphine)palladium(0) (0.01 g) were added and the mixture heated under reflux for 3 hours. The cooled reaction mixture was then poured into ether (25 ml) and water (25 ml). The organic layer was separated, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel (40 g) eluted with dichloromethane methanol (0→1%). Combination and evaporation of suitable fractions gave the title compound as a pale brown crystalline solid, m.p. 187° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 3 hours
  5. customThe cooled reaction mixture
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (40 g)
  10. washeluted with dichloromethane methanol (0→1%)
  11. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-2c88a439f7f54f5e80344ba56b1b12d2
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Reaction notes

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