Ammonia → (S)-2'-bromo-4'-fluoro-7'-methoxy-2,6-dihydrospiro[[1,4]oxazine-3,9'-xanthen]-5-amine

Participants

Reaction Conditions

Reaction Steps

In a 350-mL resealable vessel, the (S)-2′-bromo-4′-fluoro-7′-methoxyspiro[morpholine-3,9′-xanthene]-5-thione (3.0 g, 7.31 mmol) was dissolved in a dioxane solution of ammonia (0.5 M, 175 mL, 88 mmol). Mercury (II) chloride (2.98 g, 10.97 mmol) was added, and the vessel was sealed and heated in a 55° C. oil bath overnight. The reaction was cooled and then filtered through Celite, rinsing with 10% MeOH-DCM. The filtrate was concentrated, and the residue was transferred to a resealable vessel with 50 mL of dioxane. A solution of ammonia in dioxane (0.5 M, 100 mL, 50 mmol) was added, followed by mercury (II) chloride (2.0 g, 7.36 mmol). The vessel was sealed and heated in a 60° C. oil bath for 14 h. The mixture was cooled and filtered through Celite, rinsing with 10% MeOH-DCM. The filtrate was concentrated, and the residue was purified through silica gel (300 mL) using 7.5% MeOH-DCM to afford 1.33 g of (S)-2′-bromo-4′-fluoro-7′-methoxy-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-5-amine

Provenance & Evidence