Sodium Iodide → (S)-tert-butyl 5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-9-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate

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Reaction Steps

A mixture of (S)-tert-butyl 4-oxo-9-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (389 mg, 1.12 mmol), 6-bromo-1-(chloromethyl)-2-methoxynaphthalene (481 mg, 1.68 mmol), NaI (253 mg, 1.68 mmol) and Cs2CO3 (549 mg, 1.68 mmol) in DMF (15.6 mL) was stirred at RT for 6 h and diluted with EtOAc. The mixture was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated to give a residue that was purified by silica gel chromatography to afford (S)-tert-butyl 5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-9-(trifluoromethyl)-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (321 mg, 48%) as a colorless waxy solid. MS m/z 617/619 (MNa)+

Provenance & Evidence