1,2-Dichloroethane → HCID 66605774, compound

Participants

Reaction Conditions

Reaction Steps

1,2-Dichloroethane (10 mL) was added to a mixture of methyl 3-azido-2-(4-nitrophenyl)-6-(3-(trifluoromethyl)phenyl)isonicotinate (1.0 g, 2.3 mmol), rhodium octanoate dimer (0.125 g, 0.161 mmol) and crushed 4A° molecular sieves (1.0 g). The reaction was heated at 80° C. for 20 hr. The crude mixture was diluted with DCM and silica gel chromatography (step gradient elution with DCM containing 0 to 20% MeOH) afforded methyl 7-nitro-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (400 mg, 0.963 mmol, 43% yield). MS (ESI) m/z 416.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 12.24 (1H, br s), 8.42-8.72 (5H, m), 8.16 (1H, dd, J=8.55, 1.83 Hz), 7.82 (2H, ddd, J=15.11, 7.78, 7.63 Hz), 4.10 (3H, s).

Provenance & Evidence