8-Hydroxyquinoline → 1-(2-(4-ethoxyphenyl)thiazol-5-yl)-3,5-dimethylpyridin-2(1H)-one

A mixture of CuI (0.038 g, 0.20 mmol), Cs2CO3 (0.98 g, 3.00 mmol) and 8-hydroxyquinoline ligand (0.029 g, 0.20 mmol) in DMSO (2 mL) was stirred at rt for 30 min under N2. Then to the reaction mixture was added a solution of 3,5-dimethylpyridin-2(1H)-one (0.30 g, 2.40 mmol) and 5-bromo-2-(4-ethoxyphenyl)thiazole (0.57 g, 2.00 mmol) in DMSO (2 mL) via syringe. The reaction mixture was heated at 130° C. for 12 h, then cooled to rt and filtered. The filtrate was diluted with H2O (10 mL) and extracted with CH2Cl2 (20 mL×3). The combined organic phases were concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:10) to give the title compound (0.17 g, 26%). The compound was characterized by the following spectroscopic data:

1. temperatureThe reaction mixture was heated at 130° C. for 12 h
2. temperaturecooled to rt
3. filtrationfiltered
4. additionThe filtrate was diluted with H2O (10 mL)
5. extractionextracted with CH2Cl2 (20 mL×3)
6. concentrationThe combined organic phases were concentrated in vacuo
7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:10)

ORD-Eintrag

ord-0282cdf79cd446d2ad73ec2520a83efd

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09434695B2