Dichloromethane → 4-(2-(3,5-Dimethoxyphenethyl)-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazin-6-yl)picolinonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (60.0 mg, 0.119 mmol) (from Example 1, Step 4), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile (0.041 g, 0.18 mmol from Combi-Blocks), sodium carbonate (25 mg, 0.24 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (20. mg, 0.024 mmol) in acetonitrile (1 mL)/water (0.2 mL) was evacuated and the refilled with N2 and then stirred at 100° C. for 3 hours. The mixture was diluted with ethyl acetate, washed with saturated NaHCO3, water, brine, then dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-60%) to afford the desired product (0.055 g, 85%). LCMS calculated for C28H24N5O4S (M+H)+: m/z=526.2. Found 526.2.

Provenance & Evidence