Reaction #8344

Reaction equation

ethyl acetate

3-ethoxycarbonyl-5-pyridin-2-yl-4-quinolin-4-yl-pyrazole

2-bromoethanol

cesium carbonate

→

title compound

2-Pyridin-2-yl-3-quinolin-4-yl-pyrazolo[5,1-c]morpholin-4-one

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   TemperatureThe mixture is cooled to room temperature
2. 2
   WashThe organic portion is washed with water
3. 3
   Dryingdried (sodium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherThe residue is chromatographed on SiO2 (ethyl acetate/hexane)

Procedure

A mixture of 3-ethoxycarbonyl-5-pyridin-2-yl-4-quinolin-4-yl-pyrazole (0.35 g, 1.00 mmol), 2-bromoethanol (0.15 g, 1.12 mmol), and cesium carbonate (0.50 g, 1.5 mmol) in N,N-dimethylformamide (20 mL) is heated at 60° C. for 2 h. The mixture is cooled to room temperature and poured into ethyl acetate (60 mL). The organic portion is washed with water, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (ethyl acetate/hexane) to yield the title compound, 110 mg (32%).

Source