Triethylamine → HCID 10024380, compound

HRID 1032724Notes

Reaction equation

HRID 1032724 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:32][Si:33]([C:36]#[CH:37])([CH3:35])[CH3:34]>C(#N)C>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([C:37]#[C:36][Si:33]([CH3:35])([CH3:34])[CH3:32])[CH:11]=3)[C:6](=[O:24])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:8]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 10408037HCID 10408037, compound

Product 1

HCID 10024380HCID 10024380, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 25.4 g ethyl 7-bromo-1,4-dihydro-1-(4-fluorophenyl)-4-oxo-3-quinolinecarboxylate in 975 ml acetonitrile at 40°-50° C. was added 1.4 g cuprous iodide and 325 ml triethylamine. The air in the reaction was replaced by argon, and 1.4 g bis-triphenylphosphine palladium dichloride and 15.5 ml trimethylsilylacetylene were added. The reaction mixture was heated at reflux for one hour, then chilled to 0° C, and the product was collected to give 23.4 g ethyl 1,4-dihydro-1-(4-fluoro- phenyl)-4-oxo-7-(trimethylsilylethynyl)-3-quinolinecarboxylate. A sample of the compound was further purified by recrystallization from DMF to give a colorless solid, m.p. 247°-249° C. The corresponding carboxylic acid, obtained by hydrolysis of the ester with ethanolic hydrogen chloride, was obtained as a light-tan powder, m.p. 289° C. (decompn.).

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for one hour
  4. customthe product was collected

Sources & evidence

ORD record
ord-b8d45f84cb0844bf887de84ccfc7a863
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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