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

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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, 110 mg, 0.205 mmol) in tetrahydrofuran (2 mL), sodium hydride (12.0 mg, 0.300 mmol) was added at 0° C. After 10 min, [β-(trimethylsilyl)ethoxy]methyl chloride (55.7 μL, 0.315 mmol) was added dropwise. After another 1 hour, the reaction was quenched with saturated aqueous NH4Cl, extracted with methylene chloride. The combined organic layers were dried over MgSO4, and then concentrated. The residue was purified on silica gel (eluting with 0 to 8% MeOH in DCM) to give the desired product (55 mg, 31%). LCMS calculated for C33H45BrN5O3Si (M+H)+: m/z=666.2. Found: 666.3.

Provenance & Evidence