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

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 6-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (from Example 1, step 4, 30.0 mg, 59.7 μmol), 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine (from Alfa Aesar, cat# H51659, 19.8 mg, 6.57 μmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (4.9 mg, 5.97 mmol), and potassium phosphate (25.4 mg, 119 μmol) in water (0.2 mL)/1,4-dioxane (1 mL) was heated at 88° C. After another 1 hour, the reaction mixture was quenched with saturated aq. NH4Cl, extracted with methylene chloride. The combined organic layers were dried over MgSO4, then concentrated to give the desired product (25 mg, 70%). LCMS calculated for C33H36N5O4S (M+H)+: m/z=598.3. Found: 598.3.

Provenance & Evidence