Cesium carbonate → 2-(4-Chloro-phenyl)-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

HRID 271733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271733
C([O-])([O-])=O.[Cs+].[Cs+].Br[C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[N:12][CH:13]=1.[C:21]([C:23]1[CH:36]=[CH:35][C:26]([O:27][CH2:28][CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1)#[CH:22]>C1COCC1.[Cu]I>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:10]=[CH:9][C:8]([C:22]#[C:21][C:23]3[CH:24]=[CH:25][C:26]([O:27][CH2:28][CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:35][CH:36]=3)=[CH:13][N:12]=2)=[CH:15][CH:16]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 131283835-Bromo-2-(4-chlorophenyl)pyridineHCID 859698151-[2-(4-Ethynyl-phenoxy)-ethyl]-pyrrolidine

Produkt 1

HCID 598359092-(4-Chloro-phenyl)-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under an N2 atmosphere 773 mg (2.25 mmol) Cs2CO3, 14 mg (0.08 mmol) CuI and 87 mg (0.08 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 403 mg (1.5 mmol) 5-bromo-2-(4-chloro-phenyl)-pyridine and 322 mg (1.5 mmol) 1-[2-(4-ethynyl-phenoxy)-ethyl]-pyrrolidine in 10 mL THF and the reaction mixture is stirred for 4 h at RT. Then it is heated to 60° C. for 16 h. The mixture is evaporated down i.vac., the residue is combined with 30 mL water, 5 mL 3% NH3 solution and 60 mL EtOAc, the organic phase is separated off and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified first by chromatography (silica gel, EtOAc/MeOH/NH3 19:1:0.1) and then by HPLC.

Aufarbeitung

  1. temperatureThen it is heated to 60° C. for 16 h
  2. customThe mixture is evaporated down i.vac
  3. customthe organic phase is separated off
  4. dry with materialdried over Na2SO4
  5. customis purified first by chromatography (silica gel, EtOAc/MeOH/NH3 19:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-245a570b535647b6855eebd90df7650f
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452911B2

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