Triethylamine → 3-(3-nitrophenyl)-4-[(trimethylsilyl)ethynyl]-1H-pyrazole

HRID 45870

Reaction equation

HRID 45870 reaction equation
I[C:2]1[C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)=[N:4][NH:5][CH:6]=1.C(N(CC)CC)C.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>O1CCCC1.[Pd+2].[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:13]([C:9]1[CH:8]=[C:7]([C:3]2[C:2]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[CH:6][NH:5][N:4]=2)[CH:12]=[CH:11][CH:10]=1)([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 178526613HCID 178526613, compound

Product 1

HCID 1785041883-(3-nitrophenyl)-4-[(trimethylsilyl)ethynyl]-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 84124Bis(triphenylphosphine)palladium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

415 mg (1.32 mmol) of 4-iodo-3-(3-nitrophenyl)-1H-pyrazole (prepared as described in Example 27) were dissolved in 15 ml of dry tetrahydrofuran and 494 μL (3.42 mmol)of triethylamine, 80 mg (0.106 mmol) of palladium(II)-bis(triphenylphosphine) dichloride, 26 mg (0.166 mmol) of cuprous iodide and 406 μL (2.9 mmol) of trimethylsilylacetylene were added consecutively in a nitrogen atmosphere. The reaction was refluxed under stirring for 4 hours. The solvent was then removed in vacuo and the residue re-dissolved with dichloromethane and washed with water. The organic phase was dried over sodium sulphate and evaporated, affording, after trituration with diisopropylether, 300 mg (80%) of the title compound, that was employed for the next step without any further purification.

Workup

  1. temperatureThe reaction was refluxed
  2. customThe solvent was then removed in vacuo
  3. dissolutionthe residue re-dissolved with dichloromethane
  4. washwashed with water
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. customevaporated
  7. customaffording
  8. customafter trituration with diisopropylether, 300 mg (80%) of the title compound, that was employed for the next step without any further purification

Sources & evidence

ORD record
ord-9d98488750a644b8bb9aef84a54484b8
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Linked notes

Loading…