Cesium carbonate → Ethyl 5-(4-fluorobenzamido)-2-[methyl(quinolin-6-yl)amino]thiazole-4-carboxylate

Temperatur

110 °C

To a solution of ethyl 2-bromo-5-(4-fluorobenzamido)-thiazole-4-carboxylate (0.2 g, 0.50 mmol) in toluene (10 mL) was added Xantphos (0.061 g, 0.10 mmol) and Pd2(dba)3 (0.048 g, 0.040 mmol) under argon gas. To this suspension, cesium carbonate (0.344 g, 0.90 mmol) and N-methylquinolin-6-amine (0.084 g, 0.53 mmol) were added, and the mixture was heated at 110° C. for 16 h. The reaction mixture was filtered through a bed of Celite, and the celite pad was washed with ethyl acetate (3×5 mL). The filtrate was concentrated, and the crude residue was purified by silica gel column chromatography eluted with 50% EtOAc in hexane to give 0.14 g (58% yiled) of the titled compound.

1. filtrationThe reaction mixture was filtered through a bed of Celite
2. washthe celite pad was washed with ethyl acetate (3×5 mL)
3. concentrationThe filtrate was concentrated
4. customthe crude residue was purified by silica gel column chromatography
5. washeluted with 50% EtOAc in hexane

ORD-Eintrag

ord-60225ea68c3c418a8d6f03ad8992ada3

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09102637B2