Water → HCID 9803320, compound

HRID 1108803Notes

Reaction equation

HRID 1108803 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:22](=[O:25])([O-])[OH:23].[Na+].CCOCC.O.[C:33]1(C)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(O)C>[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:33]1[CH:38]=[CH:37][C:36]2[O:23][CH2:22][O:25][C:35]=2[CH:34]=1

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 9803320HCID 9803320, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a rapidly stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (0.894 g) in toluene (4 ml) containing tetrakis(tnrphenylphosphine)palladium(0) (0.04 g) was added saturated aqueous sodium hydrogen carbonate solution (3 ml) and a solution of 3.4-methylenedioxypheny,lboronic acid (0.600 g) in ethanol (2 ml). The mixture was heated under reflux for 4 hours, cooled and then poured into ether (40 ml) and water (40 ml). The organic layer was separated, washed with water (2×30 ml), brine (30 ml) and then dried (MgSO4) and evaporated. The residue %as purified by column chromatography on silica gel (30 g) eluted with dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a pale brown crystalline solid, m.p. 222° C. with softening at 198° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. customThe organic layer was separated
  5. washwashed with water (2×30 ml), brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue %as purified by column chromatography on silica gel (30 g)
  9. washeluted with dichloromethane
  10. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-fe2619a2d9ad4995b40d342869f94f3b
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Reaction notes

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