Reaktion #69483

Reaktionsgleichung

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

Ausbeute 41.1%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting suspension was degassed with argon
2. 2
   Temperaturthen cooled to room temperature
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   workup.DISSOLUTIONThe crude product was dissolved in DMA (2 mL)
6. 6
   Sonstigepurified by preparative HPLC
7. 7
   workup.ADDITIONThe fractions containing the desired compound
8. 8
   Sonstigewere evaporated to dryness

Vorschrift

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.

Quelle