Diethyl Ether → HCID 9803320, compound

HRID 1274323Notes

Reaction equation

HRID 1274323 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+].[CH2:27]1[O:35][C:34]2[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][C:29]=2[O: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:32]1[CH:31]=[CH:30][C:29]2[O:28][CH2:27][O:35][C:34]=2[CH:33]=1

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 9803320HCID 9803320, 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 (0.894 g) in toluene (4 ml) containing tetrakis(triphenylphosphine)palladium(0) (0.04 g) was added saturated aqueous sodium hydrogen carbonate solution (3 ml) and a solution of 3,4-methylenedioxyphenylboronic 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 was 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 was 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-b2192acfa9384eb0afbd98870afabfd8
Source dataset
uspto-grants-2000_12
Patent number
US06156782

Reaction notes

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