Triethylamine → HCID 178477995, compound

HRID 2359026Notes

Reaction equation

HRID 2359026 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=O)[C:8]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:9][N:10](C)C)=[CH:4][CH:3]=1.O.NN.C([N:25](CC)CC)C>C(O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:8]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:9][NH:10][N:25]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 67258869HCID 67258869, compound

Product 1

HCID 178477995HCID 178477995, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(5-chloro-2-thienyl)-3-(dimethylamino)-2-(pyridin-4-yl)prop-2-en-1-one (5.1 mmol), hydrazine hydrate (7.6 mmol) and triethylamine (7.6 mmol) in 25 mL ethanol was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel (dichloromethane:methanol 50:1 to 20:1) to afford 1.16 g 4-[3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (83% yield).

Workup

  1. temperaturewas refluxed for 3 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by chromatography on silica gel (dichloromethane:methanol 50:1 to 20:1)

Sources & evidence

ORD record
ord-35a18591063d4b50b3151267f29689aa
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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