Diethyl Ether → HCID 22120916, compound

HRID 1108808Notes

Reaction equation

HRID 1108808 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+].[CH3:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O.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:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[CH3:27]

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 27332672-Methylphenyl boronic acidHCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 22120916HCID 22120916, compound

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 (1 g) in toluene (6 ml) containing tetrakis(triphenylphosphine)palladium(0) (0.05 g) was added saturated aqueous sodium hydrogen carbonate solution (3 ml) and a solution of 2-methylphenylboronic acid (0.610 g) in ethanol (3 ml). The mixture was heated under reflux for 24 hours, cooled and then poured into ether (60 ml) and water (80 ml). The layers were separated and the aqueous phase extracted with a second portion of ether (60 ml). The combined organic layers were washed with water (2×50 ml), brine (50 ml) and then dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel (50 g) eluted with ether:hexane (3:2). Combination and evaporation of suitable fractions gave the title compound as a pale brown crystalline solid, m.p. 199-202° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperaturecooled
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with a second portion of ether (60 ml)
  6. washThe combined organic layers were washed with water (2×50 ml), brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (50 g)
  10. washeluted with ether:hexane (3:2)
  11. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-59c52ecd3205408089a477c7b62b4e6a
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Reaction notes

Loading…