1,2-Dichloroethane → methyl 2-bromo-7-(4-morpholinyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

1,2-Dichloroethane (0.4 mL) was added to a mixture of methyl 3-azido-6-bromo-6′-morpholino-2,3′-bipyridine-4-carboxylate (240 mg, 0.572 mmol), rhodium octanoate dimer (35.7 mg, 0.046 mmol) and crushed 4 A° molecular sieves (500 mg gm) and heated overnights at 80° C. The reaction was diluted with THF and filtered. The collected solid was washed with multiple portions of boiling THF to extract all of the product. The solvent was removed from the combined filtrates and the residue was suspended in MeOH and the product was collected by filtration. This left methyl 2-bromo-7-(4-morpholinyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylate (167 mg, 0.427 mmol, 745% yield) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 11.75 (1H, s), 8.30 (1H, d, J=8.85 Hz), 7.72 (1H, s), 6.91 (1H, d, J=8.85 Hz), 4.01 (3H, s), 3.74 (8H, dd, J=15.56, 4.88 Hz).

Provenance & Evidence