Triethylamine → 3-{2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazin-6-yl}-N,N-diethylprop-2-yn-1-amine

Participants

Reaction Conditions

Reaction Steps

A solution of N,N-diethylprop-2-yn-1-amine (10.6 mg, 95.5 μmol), bis(triphenylphosphine)palladium(II) chloride (2.8 mg, 4.0 μmol), copper(I) iodide (1.2 mg, 6.4 mmol), triethylamine (17.0 μL, 120 μmol), and 6-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (from Example 1, Step 4, 40.0 mg, 79.7 μmol) in N,N-dimethylformamide (1.0 mL) was stirred at ambient temperature overnight. The reaction was quenched with saturated aq. NH4Cl, then extracted with methylene chloride. The combined organic layers were dried over MgSO4, and then concentrated. The residue was dissolved in methanol (2.0 mL) and potassium carbonate (22.0 mg, 0.159 mmol) was added. The reaction mixture was then warmed up to 60° C. After 1 hour, the crude mixture was allowed to warm to room temperature and was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min) to give the desired product (6.0 mg, 20%) as its TFA salt. LCMS calculated for C23H29N4O2 (M+H)+: m/z=393.2. Found: 393.1.

Provenance & Evidence