Diethyl Ether → HCID 22120908, compound

HRID 1108805Notes

Reaction equation

HRID 1108805 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+].[Cl: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]([Cl:27])[CH:33]=1

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 22120908HCID 22120908, compoundYield 21.6%

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 (0.335 g) in toluene (2 ml) containing tetrakis(triphenylphosphine)palladium(0) (0.03 g) was added saturated aqueous sodium hydrogen carbonate solution (1 ml) and a solution of 3-chlorophenylboronic acid (0.240 g) in ethanol (1 ml). The mixture wAas heated under reflux for 4 hours, cooled and then poured into ether (25 ml) and water (25 ml). The organic layer was separated, washed with water (25 ml), brine (25 ml) and then dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (40 g) eluted with dichloromethane. Combination and evaporation of suitable fractions gave a white solid (70 mg) which was further purified by HPLC. Combination and processing of suitable fractions gave the title compound as a white crystalline solid, m.p. 161-2° C.

Workup

  1. temperatureThe mixture wAas heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. customThe organic layer was separated
  5. washwashed with water (25 ml), brine (25 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (40 g)
  9. washeluted with dichloromethane
  10. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-4a80900e3f2e48e490cee6d459f98a54
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Reaction notes

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