Trifluoroacetic acid → Trifluoroacetate

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 21A (400 mg, 0.94 mmol), N-benzyl-6-bromopyrazin-2-amine (297 mg, 1.12 mmol), bis(triphenylphosphine)palladium(ii) chloride (66 mg, 0.094 mmol), tricyclohexylphosphine (26 mg, 0.094 mmol) and cesium carbonate (921 mg, 2.8 mmol) was purged with nitrogen, then anhydrous dioxane (50 mL) was added. The mixture was heated at 100° C. overnight. The reaction was cooled to room temperature and filtrated; and the solid was washed with dichloromethane (200 mL). The filtrate was concentrated and purified by flash chromatography on silica gel using an ISCO Companion eluting with heptanes/ethyl acetate (30%) to give Boc-protected intermediate that was dissolved in CH2Cl2 (10 mL) then treated with trifluoroacetic acid (1 mL). The mixture was stirred at room temperature for 5 hours and concentrated. The residue was purified by reverse-phase HPLC on Zorbax XDB C-18 using a gradient of 5-40% acetonitrile/water (containing 0.1% trifluoroacetic acid) to afford the title compound as trifluoroacetate salt. MS (DCI/NH3) m/z 385 (M+H)+.

Provenance & Evidence