Reacción #69483

Ecuación de reacción

N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide

1-bromo-3-fluorobenzene

(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine)

cesium carbonate

→

8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide

Rendimiento 41.1%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting suspension was degassed with argon
2. 2
   Temperaturathen cooled to room temperature
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   workup.DISSOLUTIONThe crude product was dissolved in DMA (2 mL)
6. 6
   Otropurified by preparative HPLC
7. 7
   workup.ADDITIONThe fractions containing the desired compound
8. 8
   Otrowere evaporated to dryness

Procedimiento

Diacetoxypalladium (3.9 mg, 0.02 mmol) was added to a stirred mixture of N,N-dimethyl-2-morpholino-4-oxo-8-(pyrrolidin-2-yl)-4H-chromene-6-carboxamide (130 mg, 0.35 mmol), 1-bromo-3-fluorobenzene (0.049 ml, 0.44 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20.25 mg, 0.03 mmol) and cesium carbonate (171 mg, 0.52 mmol) dissolved in 1,4-dioxane (4 mL). The resulting suspension was degassed with argon and stirred at 100° C. for 16 h then cooled to room temperature, filtered and concentrated. The crude product was dissolved in DMA (2 mL) and purified by preparative HPLC. The fractions containing the desired compound were evaporated to dryness to afford 8-(1-(3-fluorophenyl)pyrrolidin-2-yl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (67 mg, 41%) as a solid.

Fuente