Triethylamine → HCID 67497960, compound

HRID 1920120Notes

Reaction equation

HRID 1920120 reaction equation
[C:1]1([N:7]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[CH:10]=[C:9]([C:22]3[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31].C(N(CC)CC)C>C1COCC1.[Cu](I)I>[C:1]1([N:7]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[CH:10]=[C:9]([C:22]3[CH:27]=[CH:26][C:25]([C:34]#[C:33][Si:30]([CH3:32])([CH3:31])[CH3:29])=[CH:24][CH:23]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 67498689HCID 67498689, compound

Product 1

HCID 67497960HCID 67497960, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

After charging 9.6 parts of 1-phenyl-3-(4-iodophenyl)-5-(4-t-butylphenyl)pyrazoline synthesized by a known method, 2.4 parts of trimethylsilylacetylene, 0.28 parts of bis(triphenylphosphine)palladium(II) dichloroide, 0.04 parts of copper iodide and 40 mL of triethylamine in 80 mL of THF, the mixture was stirred at 60° C. for 10 hours. The reaction mixture was filtered, the obtained filtrate was concentrated, and the precipitate was filtered, washed, recrystallized from methanol and dried at 60° C. to obtain 5.6 parts of 1-phenyl-3-(4-trimethylsilylethynylphenyl)-5-(4-t-butylphenyl)pyrazoline having a melting point of 160-162° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe obtained filtrate was concentrated
  3. filtrationthe precipitate was filtered
  4. washwashed
  5. customrecrystallized from methanol
  6. customdried at 60° C.

Sources & evidence

ORD record
ord-b61e547fae864768b31e1dbd3ee2e087
Source dataset
uspto-grants-2012_05
Patent number
US08168796B2

Reaction notes

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