Sodium Iodide → [(S)-1-(5-Bromo-2-methoxy-naphthalen-1-ylmethyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-carbamic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

To a stirred solution of ((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester (Intermediate 2) (500 mg, 1.805 mmol) in THF (10 mL) at −78° C. was added LiHMDS (1 M in THF, 2.3 mL, 2.3 mmol) dropwise over 5 min. The mixture was stirred at −78° C. for 20 min. and a mixture of sodium iodide (295.8 mg, 1.986 mmol) and 5-bromo-1-chloromethyl-2-methoxy-naphthalene (617.3 mg, 2.166 mmol) in THF (5 mL), was added dropwise over 5 min. The mixture was stirred at −78° C. for 50 min. and the cooling bath was removed. After 16 h, aqueous citric acid was added and the mixture extracted with ethyl acetate. The extract was washed with saturated sodium carbonate solution, dried and concentrated to give a material which was purified by silica gel chromatography to provide the title compound (780 mg, 82%) as a white solid. LC-MS: 528 (M+H).

Provenance & Evidence