반응 #66756

반응 방정식

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

용매

dioxane

CHCl3

H2O

반응 조건

후처리

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

실험 절차

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.

출처