Triethylamine → HCID 67497910, compound

HRID 1920119Notes

Reaction equation

HRID 1920119 reaction equation
[C:1]1([N:7]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=3)[CH:10]=[C:9]([C:19]3[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28].C(N([CH2:37][CH3:38])CC)C>C1COCC1.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.[Cu](I)I>[C:1]1([N:7]2[CH:11]([C:12]3[CH:17]=[CH:16][C:15]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])=[CH:14][CH:13]=3)[CH:10]=[C:9]([C:19]3[CH:24]=[CH:23][C:22]([C:38]#[C:37][Si:27]([CH3:29])([CH3:28])[CH3:26])=[CH:21][CH:20]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 67498142HCID 67498142, compound

Product 1

HCID 67497910HCID 67497910, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
66 °C

Procedure

After charging 4.6 parts of 1-phenyl-3,5-di(4-bromophenyl)pyrazoline synthesized by a known method, 2.4 parts of trimethylsilylacetylene, 0.46 parts of tetrakis(triphenylphosphine)palladium(0), 0.038 parts of copper iodide and 20 ml of triethylamine in 40 ml of THF, the mixture was stirred at 66° C. for 8 hours and then the reaction mixture was filtered and washed with THF. The obtained filtrate was concentrated, and the precipitate was filtered, washed, recrystallized from methanol and dried at 60° C. to obtain 4.4 parts of 1-phenyl-3,5-di(4-trimethylsilylethynylphenyl)pyrazoline having a melting point of 108-110° C.

Workup

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

Sources & evidence

ORD record
ord-3e28aefd8ca748a89f7195588923ef62
Source dataset
uspto-grants-2012_05
Patent number
US08168796B2

Reaction notes

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