反应详情

温度

70 °C

In a 25 mL round-bottomed flask, 3-trifluoromethanesulfonyloxy-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (780 mg, 2.46 mmol, Eq: 1.00) was combined with THF (20 ml) to give a colorless solution. The solution was purged with argon for 10 min. Potassium carbonate (1.72 g, 12.3 mmol, Eq: 5.0), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (649 mg, 2.95 mmol, Eq: 1.20), tetrakis(triphenylphosphine)palladium(0) (28.4 mg, 24.6 μmol, Eq: 0.01) and water (200 μl) 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, 40 g, 50% (60:10:1 DCM:MeOH:NH4OH)/DCM) to give 3-(6-amino-pyridin-3-yl)-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (538 mg, 84%). LC/MS-ESI observed [M+H]+ 262.

1. customto give a colorless solution
2. customThe solution was purged with argon for 10 min
3. extractionextracted twice with Et2O
4. washThe organic layer was washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. customThe crude material was purified by flash chromatography (silica gel, 40 g, 50% (60:10:1 DCM:MeOH:NH4OH)/DCM)