Diisopropylethylamine → N-{2-[5-(4-Ethoxy-phenylethynyl)-pyridin-2-yl]-ethyl}-acetamide

HRID 76203

Reaktionsgleichung

CCN(C(C)C)C(C)C.Br[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])=[N:15][CH:16]=1.[CH2:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]#[CH:33])=[CH:28][CH:27]=1)[CH3:24]>CCOC(C)=O.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]#[C:33][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])=[N:15][CH:16]=2)=[CH:28][CH:27]=1)[CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

0.55 mL (3.91 mmol) DIPEA is added to 190 mg (0.78 mmol) N-[2-(5-bromo-pyridin-2-yl)-ethyl]-acetamide (I48.1), 3.72 mg (0.02 mmol) CuI and 13.7 mg (0.02 mmol) bis(triphenylphosphin)palladium-(II)-chloride. 171 mg (1.17 mmol) 4-ethoxyphenylacetylene are added and the reaction mixture is heated for 10 min at 80° C. in a microwave oven. The mixture is diluted with EtOAc and washed with water (1×) and diluted aq. ammonia solution. The organic layer is dried with MgSO4 and the solvent is removed in vacuo. The residue is purified by HPLC (MeOH/H2O/NH3).

Aufarbeitung

washwashed with water (1×) and diluted aq. ammonia solution
dry with materialThe organic layer is dried with MgSO4
customthe solvent is removed in vacuo
customThe residue is purified by HPLC (MeOH/H2O/NH3)

Quellen und Nachweise

ORD-Eintrag: ord-51640ff832fb4083add4a8d495683a8a
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08835472B2

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