反应详情

温度

105 °C

A mixture of tert-Butyl 2-chloropyridin-4-yl(3-nitrophenyl)carbamate (3.65 g, 10.43 mmol), methyl-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-3-carboxylate (5.48 g, 21.82 mmol), xantphos (0.72 g, 1.25 mmol) and Pd2dba3 (0.72 g, 0.79 mmol) was added to a thick walled reaction vessel and purged with N2. A solution of 2M K2CO3 (8.76 mL) was added, followed by dioxane (67 mL). The reaction vessel was sealed and the mixture stirred at 105° C. for 18 h. The reaction vessel was cooled to rt and the mixture was filtered over celite, washing with EtOAc. The filtrate was concentrated to afford a dark oil, which was purified via column chromatography eluting with 30-50% EtOAc/hexanes to afford methyl 5-(4-(tert-butoxycarbonyl(3-nitrophenyl)amino)pyridine-2-yl)-1H-pyrrole-3-carboxylate (2.98 g, 65% yield) as an orange oil.

1. additionwas added to a thick walled reaction vessel
2. custompurged with N2
3. additionA solution of 2M K2CO3 (8.76 mL) was added
4. customThe reaction vessel was sealed
5. temperatureThe reaction vessel was cooled to rt
6. filtrationthe mixture was filtered over celite
7. washwashing with EtOAc
8. concentrationThe filtrate was concentrated
9. customto afford a dark oil, which
10. customwas purified via column chromatography
11. washeluting with 30-50% EtOAc/hexanes