Reaction #69480

Reaction equation

8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid

DIPEA

morpholine

water

→

8-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one

Yield 79.5%

Solvents

DCM

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 15 mins
2. 2
   Extractionextracted with DCM
3. 3
   WashThe combined organic layers were washed with water
4. 4
   Washthe organic layer was washed with brine
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Concentrationconcentrated

Procedure

N-propylphosphonic acid anhydride, cyclic trimer (50 wt % solution in EtAc) (8.57 ml, 14.68 mmol) was added at room temperature in one portion to a stirred solution of 8-bromo-2-morpholino-4-oxo-4H-chromene-6-carboxylic acid (2 g, 5.65 mmol), DIPEA (4.9 mL, 28.2 mmol) and morpholine (0.543 mL, 6.2 mmol) in DCM (14 mL). The mixture was stirred at room temperature for 1 h then water (1 mL) was then added. The reaction mixture was stirred for 15 mins and extracted with DCM. The combined organic layers were washed with water; the organic layer was washed with brine, dried over magnesium sulfate and concentrated to afford 8-bromo-6-(morpholine-4-carbonyl)-2-morpholino-4H-chromen-4-one (1.90 g, 79%) as a beige solid. Mass Spectrum: m/z [M+H]+=423.

Source