Trimethylsilylacetylene → 6-(4-Chloro-benzoyl)-1-cyclopropylmethyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one

HRID 1597480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1597480
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][CH:19]2[CH2:21][CH2:20]2)[C:13](=[O:22])[CH:12]=[C:11]3[C:23]2[CH:28]=[CH:27][CH:26]=[C:25](I)[CH:24]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:32][Si:33]([C:36]#[CH:37])([CH3:35])[CH3:34]>CN(C=O)C.C(NCC)C.[Cu]I>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:18][CH:19]2[CH2:21][CH2:20]2)[C:13](=[O:22])[CH:12]=[C:11]3[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:37]#[C:36][Si:33]([CH3:35])([CH3:34])[CH3:32])[CH:24]=2)=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 185164516-(4-Chloro-benzoyl)-1-cyclopropylmethyl4-(3-iodo-phenyl)-1H-quinolin-2-one

Produkt 1

HCID 185164466-(4-Chloro-benzoyl)-1-cyclopropylmethyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 86589549DMF DiethylamineLösungsmittel

Versuchsvorschrift

A solution of 6-(4chloro-benzoyl)-1-cyclopropylmethyl-4-(3-iodo-phenyl)-1H-quinolin-2-one (4.0 g, 7.41 mmol) in DMF/diethylamine (1:1, 80 mL) was treated with palladium (II) bis(triphenyl)phosphine chloride (0.26 9, 0.37 mmol), trimethylsilylacetylene (1.09 g, 11.1 mmol), and copper (I) iodide (0.21 g, 1.09 mmol). The reaction mixture was stirred at room temperature for 3 hours, concentrated in vacuo, poured into H2O (450 mL), and filtered to give a crude brown foam. Purification by flash column chromatography (silica, ether:petroleum ether 1:1) gave 6-(4-Chloro-benzoyl)-1-cyclopropylmethyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one (3.47 g, 92%) as a yellow solid.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionpoured into H2O (450 mL)
  3. filtrationfiltered
  4. customto give a crude brown foam
  5. customPurification by flash column chromatography (silica, ether:petroleum ether 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-e5356679358f4b178053ebffa0a861bf
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06294552B1

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