Cesium carbonate → N-[3-bromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide

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A mixture of 3,4-dibromo-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-pyrrolo[2,3-b]pyridine (D3) (1.020 g, 2.51 mmol), xantphos (0.218 g, 0.377 mmol), palladium(II) acetate (0.042 g, 0.188 mmol), cesium carbonate (1.636 g, 5.02 mmol) and 3-chlorobenzenesulfonamide (0.602 g, 3.14 mmol) in 1,4-dioxane (15 mL) was stirred at 100° C. for ca. 3 hours. The mixture was evaporated to dryness and the residues partitioned between water (15 mL) and ethyl acetate (40 mL). The aqueous phase was separated and extracted with additional ethyl acetate (15 mL). The organic extracts were combined, washed with brine (10 mL), dried with MgSO4 and evaporated to dryness. The residue was purified through silica gel, eluting with a gradient of 0-40% ethyl acetate in cyclohexane to give the title compound (407.4 mg). LCMS (A): m/z (M−H)− 514/516, C19H23BrClN3O3SSi requires 515/517 (acidic).

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