7-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine → 2-[2-(3,5-dimethoxyphenyl)ethyl]-7-methyl-6-[4-(4-methylpiperazin-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5H-pyrrolo[2,3-b]pyrazine (from Example 46, 20.0 mg, 37.3 μmol) and Pd(dppf)Cl2 (2.7 mg, 3.7 μmol) in 1,4-dioxane (0.8 mL), dimethylzinc (2.0 M in toluene, 47 μL, 94.0 μmol) was added at ambient temperature. The reaction mixture was then warmed up to 90° C. After 4 hours, the volatiles were removed and the residue 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 (4.2 mg) as its TFA salt. LCMS calculated for C28H34N5O2 (M+H)+: m/z=472.2. Found: 472.2.

Provenance & Evidence