Diethylamine → HCID 19356468, compound

HRID 1641893Notes

Reaction equation

HRID 1641893 reaction equation
I[C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[CH3:7][Si:8]([C:11]#[CH:12])([CH3:10])[CH3:9].C(NCC)C>C1COCC1.[Pd](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.[Cu](I)I>[CH3:7][Si:8]([C:11]#[C:12][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1)([CH3:10])[CH3:9]

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 66111TrimethylsilylacetyleneHCID 770224-Iodopyrazole

Product 1

HCID 19356468HCID 19356468, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Iodo-1H-pyrazole (20.0 g, 103 mmol) is dissolved in anhydrous THF (150 ml) and trimethylsilyl acetylene (72.8 ml, 515 mmol) is added under an inert atmosphere. Diethyl-amine (150 ml), bis-(triphenylphosphine) palladium (II) chloride (10.8 g, 15 mmol) and copper iodide (2.9 g, 15 mmol) are added and the reaction mixture is left to stir at room temperature for 3 hours. The solvent is removed under reduced pressure. The residue is dissolved in diethyl ether and the insoluble impurities are filtered off. The solvent is removed under reduced pressure. The residue is dissolved in methanol and the insoluble impurities removed. The solvent is removed under reduced pressure. The residue is purified by dry flash chromatography on silica gel eluting with a gradient system of diethyl ether: iso-hexane (20:80 to 100:0) to afford the title compound [MH+] 165.07 1H NMR (DMSO): 0.00 (s, 9H), 7.45 (s, 1H), 7.90 (s, 1H), 12.90 (br s, 1H)

Workup

  1. waitthe reaction mixture is left
  2. customThe solvent is removed under reduced pressure
  3. dissolutionThe residue is dissolved in diethyl ether
  4. filtrationthe insoluble impurities are filtered off
  5. customThe solvent is removed under reduced pressure
  6. dissolutionThe residue is dissolved in methanol
  7. customthe insoluble impurities removed
  8. customThe solvent is removed under reduced pressure
  9. customThe residue is purified
  10. dry with materialby dry flash chromatography on silica gel eluting with a gradient system of diethyl ether: iso-hexane (20:80 to 100:0)

Sources & evidence

ORD record
ord-18fdcb165ec54c46864c95cd6c63ccef
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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