1,2-Dichloroethane → HCID 86663060, compound

Participants

Reaction Conditions

Reaction Steps

1,2-Dichloroethane (14 mL) was added to a mixture of methyl 3-azido-6-bromo-2-(4-morpholinophenyl)isonicotinate (4.66 g, 11 1 mmol), rhodium octanoate dimer (0.521 g, 0.669 mmol) and crushed 4A° molecular sieves (4.66 g) and this was heated at 85° C. for 26 hr. It was diluted with DCM, filtered, and the solid was washed with multiple portions of DCM. The solvent was removed from the combined filtrate and the residue was suspended in MeOH. The solid was collected by filtration, washed with MeOH, and dried to leave methyl 2-bromo-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxylate (4.05 g, 10.4 mmol, 93% yield) as a yellow solid. MS (ESI) m/z 390.11 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.43 (1H, br. s.), 8.20 (1H, d, J=8.85 Hz), 7.86 (1H, s), 7.00 (1H, dd, J=8.70, 1.68 Hz), 6.89 (1H, s), 4.06 (3H, s), 3.91-3.96 (4H, m), 3.32-3.37 (4H, m).

Provenance & Evidence