반응 #536811

반응 방정식

NaHCO3

Potassium carbonate

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

3-trifluoromethanesulfonyloxy-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

→

tert-butyl 3-(6-aminopyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

수율 54.4%

용매

water

THF

반응 조건

후처리

1. 1
   기타to give a colorless solution
2. 2
   기타The solution was purged with argon for 10 min
3. 3
   추출extracted twice with Et2O
4. 4
   세척The organic layer was washed with brine
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated in vacuo
7. 7
   기타The crude material was purified by flash chromatography (silica gel, 60 g, 50% (60:10:1 DCM:MeOH:NH4OH)/DCM)

실험 절차

In a 250 mL round-bottomed flask, 3-trifluoromethanesulfonyloxy-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (2.3 g, 7.25 mmol, Eq: 1.00) was combined with THF (60 ml) to give a colorless solution. The solution was purged with argon for 10 min. Potassium carbonate (5.06 g, 36.2 mmol, Eq: 5.0), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1.91 g, 8.7 mmol, Eq: 1.20), tetrakis(triphenylphosphine)palladium(0) (83.8 mg, 72.5 μmol, Eq: 0.01) and water (1.2 ml) were added. The reaction mixture was heated to 70° C. and stirred for 16 h. The reaction mixture was poured into saturated NaHCO3 and extracted twice with Et2O. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 60 g, 50% (60:10:1 DCM:MeOH:NH4OH)/DCM) to give tert-butyl 3-(6-aminopyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (1.03 g, 54%). LC/MS-ESI observed [M+H]+ 262.

출처