反应详情

温度

60 °C

1,2-Dichloroethane (3.5 mL) was added to a mixture of methyl 3-azido-2-(4-(benzyloxy)phenyl)-6-bromoisonicotinate (2.28 g, 5.19 mmol), rhodium octanoate dimer (0.101 g, 0.130 mmol) and crushed 4 A° molecular sieves (2.2 gm). This was heated at 60° C. for 6 hr. The reaction was diluted with a mixture of DCM:MeOH=3:1 and filtered. The collected solid was washed with additional DCM:MeOH mixture to dissolve any remaining product. The solvent was removed from the filtrate and the residue was suspended in MeOH. The product was collected by filtration and washed with a little MeOH to leave methyl 7-(benzyloxy)-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (1.72 g, 4.18 mmol, 81% yield) as a yellow solid. MS (ESI) m/z 412.9 (M+H). 1H NMR (400 MHz, chloroform-d) δ ppm 9.45 (1H, br. s.), 8.22 (1H, d, J=8.81 Hz), 7.87 (1H, s), 7.43-7.50 (2H, m), 7.37-7.44 (2H, m), 7.30-7.37 (1H, m), 6.96-7.06 (2H, m), 5.18 (2H, s), 4.04 (3H, s).

1. customcrushed 4 A° molecular sieves (2.2 gm)
2. filtrationMeOH=3:1 and filtered
3. washThe collected solid was washed with additional DCM
4. dissolutionMeOH mixture to dissolve any remaining product
5. customThe solvent was removed from the filtrate
6. filtrationThe product was collected by filtration
7. washwashed with a little MeOH