Triethylamine → HCID 21188084, compound

HRID 1383585Notes

Reaction equation

HRID 1383585 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([S:14][C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=2[Cl:19])[N:5]=[C:4]([C:20]#[N:21])[C:3]=1I.C(N(CC)CC)C.[CH3:30][Si:31]([C:34]#[CH:35])([CH3:33])[CH3:32]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([S:14][C:15]([F:18])([F:17])[F:16])=[CH:9][C:8]=2[Cl:19])[N:5]=[C:4]([C:20]#[N:21])[C:3]=1[C:35]#[C:34][Si:31]([CH3:33])([CH3:32])[CH3:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 21188067HCID 21188067, compound

Product 1

HCID 21188084HCID 21188084, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylsulphenylphenyl)4-iodopyrazole (10 g) in dimethylformamide (45 ml) at room temperature was added triethylamine (34 ml), trimethylsilylacetylene (6 ml), cuprous iodide (0.4 g), and bis(triphenylphosphine)palladium(II) chloride (0.4 g). The mixture was heated at 75° C. for 6 hours. The cooled reaction mixture was evaporated to dryness and the residue partitioned between water and dichloromethane. The organic layer was separated and washed with water, then brine, and then dried (Na2SO4) and evaporated to give the crude product which was purified by column chromatography on silica gel (400 g) eluting with dichloromethane. Combination and evaporation of suitable fractions provided an oily solid which was further purified by column chromatography on silica gel (400 g) eluting with dichloromethane/hexane. Combination and evaporation of suitable fractions followed by recrystallisation of their residue from dichloromethane/hexane provided the title compound as a buff solid m.p. 165-169° C.

Workup

  1. customThe cooled reaction mixture
  2. customwas evaporated to dryness
  3. customthe residue partitioned between water and dichloromethane
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialbrine, and then dried (Na2SO4)
  7. customevaporated
  8. customto give the crude product which
  9. customwas purified by column chromatography on silica gel (400 g)
  10. washeluting with dichloromethane
  11. customCombination and evaporation of suitable fractions
  12. customprovided an oily solid which
  13. customwas further purified by column chromatography on silica gel (400 g)
  14. washeluting with dichloromethane/hexane
  15. customCombination and evaporation of suitable fractions
  16. customfollowed by recrystallisation of their residue from dichloromethane/hexane

Sources & evidence

ORD record
ord-4977b63e8e6a477e88570069565e305f
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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