Boron tribromide → HCID 90308628, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask was charged with N-((4aR,6S,11bR)-2-amino-3,3,6,11b-tetramethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-10-yl)-5-chloro-3-(methoxymethyl)picolinamide (125 mg, 0.240 mmol) and DCM (2.4 ml), and the solution was cooled to 0° C. under nitrogen. BBr3 (47.6 μl, 0.504 mmol) was added dropwise, and the mixture was allowed to warm to RT. After stirring at RT for 1 h, the reaction was quenched with water and neutralized with saturated aqueous sodium bicarbonate. EtOAc was added, and the layers were separated. The aqueous portion was extracted with additional EtOAc, and the combined organic portions were dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography using a gradient of 0-75% 75/25/2 EtOAc/EtOH/NH4OH in heptane to provide N-((4aR,6S,11bR)-2-amino-3,3,6,11b-tetramethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-10-yl)-5-chloro-3-(hydroxymethyl)picolinamide (30 mg, 0.059 mmol, 24.66% yield) as a tan solid. LC/MS (ESI+) m/z=507.0 (M+H).

Provenance & Evidence