1,2-Dichloroethane → HCID 86663042, compound

Participants

Reaction Conditions

Reaction Steps

1.2-Dichloroethane (4.4 mL) was added to a mixture of methyl 3-azido-6-bromo-2-(4-chlorophenyl)isonicotinate (2.42 g, 6.58 mmol), rhodium octanoate dimer (0.41 g, 0.53 mmol) and crushed 4A° molecular sieves (2.5 gm) and heated at 80° C. for 24 hr. The reaction was diluted with THF and filtered. The collected solid was washed with multiple portions of hot THF to extract remaining product. The solvent was removed from the combined filtrates and the residue was suspended in MeOH and the product was collected by filtration to leave methyl 2-bromo-7-chloro-5H-pyrido[3,2-b]indole-4-carboxylate (1.92 g, 5.65 mmol, 86% yield) as a gray solid. MS (ESI) m/z 340.99 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.89 (1H, s), 8.19 (1H, d, J=8.24 Hz), 7.92 (1H, s), 7.76 (1H, d, J=1.53 Hz), 7.35 (1H, dd, J=8.55, 1.83 Hz), 4.04 (3H, s).

Provenance & Evidence