Toluene → HCID 89573714, compound

Participants

Reaction Conditions

Reaction Steps

Dioxane (1 mL) and water (0.1 mL) were added to a mixture of tert-butyl rel-((4aS,10bS)-9-bromo-10b-methyl-4a,5,6,10b-tetrahydro-4H-naphtho[1,2-d][1,3]thiazin-2-yl)carbamate from preparation C (10 mg, 0.024 mmol), (1H-pyrazol-4-yl)boronic acid (27.2 mg, 0.243 mmol) and potassium carbonate (33.6 mg, 0.243 mmol). Nitrogen was bubbled through the mixture for 5 min. 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) dichloride, toluene (10 mg, 0.012 mmol) was added and the resulting mixture was heated at 100° C. for 1 h. The reaction contents were cooled to rt and were transferred to a separatory funnel containing saturated aqueous NaHCO3 solution (10 mL). The aqueous layer was extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The crude product of step 19A was used in the next step without further purification. LCMS (M+H)+=399.08.

Provenance & Evidence