Methyl 3-azido-6-bromo-2-(4-(morpholine-4-carbonyl)phenyl)isonicotinate → methyl 2-bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxylate

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Reaction Steps

A solution of methyl 3-azido-6-bromo-2-(4-(morpholine-4-carbonyl)phenyl)-isonicotinate (7.2 g, 16.1 mmol) in 1,2-dichlorobenzene (115 mL) was placed in a 180° C. oil bath and stirred for 10 minutes. The solvent was removed, the residue suspended in methylene chloride, and the solid collected by filtration. This was resuspended in methylene chloride and filtered to afford methyl 2-bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxylate (3.02 gm, 45% yield). Removal of the solvent from filtrate followed by flash silica gel chromatography (step gradient elution with methylene chloride containing 0 to 3% MeOH) afforded another 1.02 gm (15% yield) of product. MS (ESI) m/z 416 and 418 (M+H). 1H NMR (MeOD) δ ppm 8.39 (1H, d, J=7.94 Hz), 8.08 (1H, s), 7.78 (1H, s), 7.41 (1H, d, J=7.93 Hz), 4.12 (3H, s), 3.61-3.95 (6H, m), 3.46-3.61 (2H, m).

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