Reaktion #66756

Reaktionsgleichung

1′-tert-butoxycarbonyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[chroman-2,4′-piperidin]-4-one

6-chloronicotinamide

Na2CO3

→

compound

tert-Butyl 6-(5-carbamoylpyridin-2-yl)-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate

Lösungsmittel

dioxane

CHCl3

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer was extracted with CHCl3
2. 2
   WaschenThe combined organic layer was washed with brine
3. 3
   Trocknendried over MgSO4 and silicagel
4. 4
   SonstigeThe desiccant was removed through celite filtration
5. 5
   Einengenthe filtrate was concentrated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by crystallization (CHCl3-EtOAc)

Vorschrift

1′-tert-butoxycarbonyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[chroman-2,4′-piperidin]-4-one (40.0 g, 90.0 mmol), 6-chloronicotinamide (17.0 g, 108 mmol), Pd(PPh3)4 (5.21 g, 4.51 mmol), and aqueous 2M Na2CO3 (100 ml) solution were suspended in dioxane (300 ml) and heated at 100° C. for 16 h. The reaction mixture was diluted with CHCl3 and H2O, the aqueous layer was extracted with CHCl3. The combined organic layer was washed with brine, dried over MgSO4 and silicagel. The desiccant was removed through celite filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by crystallization (CHCl3-EtOAc) to obtain the intended compound as a colorless solid.

Quelle