Diethyl Ether → HCID 22120917, compound

HRID 1108807Notes

Reaction equation

HRID 1108807 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][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=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:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[O:28][CH3:27]

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 27339582-Methoxyphenylboronic acidHCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Product 1

HCID 22120917HCID 22120917, 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) (0.09 g) was added saturated aqueous sodium hydrogen carbonate solution (7 ml) and a solution of 2-methoxypbenylboronic acid (1.7 g) in ethanol (3 ml). The mixture was heated under reflux for 2.5 hours, cooled and then poured into ether (60 m) and water (50 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 (2×45 ml). brine (40 ml) and then dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (60 g) eluted with ether:hexane (3:2). After combination and evaporation of suitable fractions the residue was further purified by HPLC. Combination and processing of suitable fractions gave the title compound as a white crystalline solid, m.p. 193° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 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 (2×45 ml)
  7. dry with materialbrine (40 ml) and then dried (Na2SO4)
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (60 g)
  10. washeluted with ether:hexane (3:2)
  11. customAfter combination and evaporation of suitable fractions the residue
  12. customwas further purified by HPLC

Sources & evidence

ORD record
ord-1903f699b17b4d72ac0a53db24e58363
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Reaction notes

Loading…