Triethylamine → 4-[6-(4-Chloro-phenyl)-quinoline-2-ylethynyl]-benzaldehyde

HRID 1916752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916752
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:8]=2)[N:3]=1.[C:19]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)#[CH:20].C(N(CC)CC)C>CN(C=O)C.C(#N)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([C:20]#[C:19][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=2)[CH:11]=[CH:10]3)=[CH:13][CH:14]=1

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 27716454-EthynylbenzaldehydeHCID 859696922-Bromo-6-(4-chloro-phenyl)-quinoline

Produkt 1

HCID 859696974-[6-(4-Chloro-phenyl)-quinoline-2-ylethynyl]-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere 0.6 mg CuI, 9.3 mg Pd(PPh3)2Cl2 and 318 mg (1 mmol) 2-bromo-6-(4-chloro-phenyl)-quinoline are added successively to a solution of 85 mg (0.66 mmol) 4-ethynyl-benzaldehyde and 2.6 mL (18.67 mmol) triethylamine in 5 mL absolute DMF and 10 mL acetonitrile. The reaction mixture is stirred for 14 hours at RT and evaporated down. The purification is carried out by column chromatography on silica gel (PE/EtOAc 1:1).

Aufarbeitung

  1. customevaporated down
  2. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-1fdbf28f2ce44200932e9ee827c1caea
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

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