반응 #304954

반응 방정식

product

3-Amino-6-bromo-N-(pyridin-3-yl)pyrazine-2-carboxamide

product

(3-(4-Bromophenyl)propoxy)(tert-butyl)dimethylsilane

bis(pinacolato)diboron

KOAc

Na2CO3

→

subtitle compound ( vi )

수율 62.3%

3-Amino-6-(4-(3-(tert-butyldimethylsilyloxy)propyl)phenyl)-N-(pyridin-3-yl)-pyrazine-2-carboxamide

수율 62.3%

용매

dioxane

Water

반응 조건

후처리

1. 1
   기타degassed with N2 (×3)
2. 2
   workup.STIRRINGThe mixture was stirred at 80° C. under a N2 atmosphere for 3 hours
3. 3
   workup.ADDITIONwere added
4. 4
   기타The resulting solution was degassed again with N2 (×3)
5. 5
   workup.STIRRINGThe reaction mixture was stirred at 90° C. under a N2 atmosphere for additional 10 hours
6. 6
   workup.ADDITIONNa2SO4 was added
7. 7
   여과filtered
8. 8
   농축the filtrate concentrated in vacuo
9. 9
   기타The crude product was purified by column chromatography with PE

실험 절차

A mixture of the product of step (ii) (9.84 g, 30 mmol), bis(pinacolato)diboron (11.4 g, 45 mmol), KOAc (9 g, 90 mmol) and Pd(dppf)Cl2 (1 g, 1.5 mmol) in dioxane (200 mL) was stirred and degassed with N2 (×3). The mixture was stirred at 80° C. under a N2 atmosphere for 3 hours. The reaction mixture was cooled to room temperature. Water (25 mL) and Na2CO3 (10 g, 90 mmol) were added to the mixture. The mixture was stirred for 10 minutes before the product of step (v) (7.9 g, 27 mmol) and Pd(dppf)Cl2 (0.5 g, 0.7 mmol) were added. The resulting solution was degassed again with N2 (×3). The reaction mixture was stirred at 90° C. under a N2 atmosphere for additional 10 hours. Na2SO4 was added, filtered and the filtrate concentrated in vacuo. The crude product was purified by column chromatography with PE:EtOAc=5:1 to 3:1 as eluent to afford the subtitle compound (vi) as a yellow solid (7.8 g).

출처