1,2-Dichloroethane → HCID 86663038, compound

Participants

Reaction Conditions

Reaction Steps

1,2-Dichloroethane (1.7 mL) was added to a mixture of methyl 3-azido-6-bromo-2-(3-formylphenyl)isonicotinate (903 mg, 2.50 mmol), rhodium octanoate dimer (156 mg, 0.20 mmol) and crushed 4A° molecular sieves (0.9 gm) in an flask. This was heated at 80° C. for 18 hr. The reaction was diluted THF and filtered. The collected solid was washed with multiple portions of boiling THF to complete extraction of the product. The solvent was removed from the combined filtrates, the residue was suspended in MeOH, and the product was collected by filtration. This left methyl 2-bromo-8-formyl-5H-pyrido[3,2-b]indole-4-carboxylate (484 mg, 1.45 mmol, 58% yield) as a grey solid. MS (ESI) m/z 334.91 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.25 (1H, s), 10.12 (1H, s), 8.80 (1H, s), 8.11 (1H, d, J=9.32 Hz), 7.98 (1H, s), 7.88(1H, d, J=8.56 Hz), 3.33 (3H, s).

Provenance & Evidence