Water → HCID 178489654, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (Example 33) (160 mg, 0.305 mmol) in 1,4-dioxane (2.5 mL) was added 1H-pyrazol-3-ylboronic acid (51.3 mg, 0.458 mmol), bis(triphenylphosphine)palladium(II) chloride (21.44 mg, 0.031 mmol) and potassium carbonate (127 mg, 0.916 mmol). Then, water (1 mL) was added to the mixture. The reaction mixture was then heated at 100° C. in a microwave for 15 min (×2). Extra tetrakis(triphenylphosphine)palladium(0) (35.3 mg, 0.031 mmol) was added and the mixture heated at 100° C. for another 15 min. The solvent from was then removed in vacuo and the residue dissolved in ethyl acetate (20 mL) and washed with water (20 mL). The aqueous phase was re-extracted with ethyl acetate (20 mL×2). All organic phase were combined, dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified on silica, eluting with a gradient of 0-50% ethyl acetate in cyclohexane and further purified using MDAP (acidic conditions), to give the title compound (16 mg). LCMS (A) m/z: 509 [M−1]−, Rt 1.23 min (acidic).

Provenance & Evidence