Triacetoxyperiodinane → Tert-butyl 4-(6-bromopyridin-2-yl)-6-oxo-1,4-diazepane-1-carboxylate

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Reaction Steps

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate (1.05 g, 2.83 mmol) from Examples 88, 89, 148 in DCM (35 mL) at 0° C. was added (1,1,1-triacetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (2.40 g, 5.66 mmol). The mixture was stirred overnight, quenched with brine (40 mL) and DCM (30 mL), and extracted with DCM (100 mL×3), and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/ethyl acetate (5% to 50%) as eluting solvents to afford tert-butyl 4-(6-bromopyridin-2-yl)-6-oxo-1,4-diazepane-1-carboxylate as a yellow oil (846 mg, 81%). MS (ESI) m/z: 370 [M+H]+.

Provenance & Evidence