Water → 1,1-Dimethylethyl 4-[3-(4-amino-2,6-dimethylthieno[2,3-b]pyridin-3-yl)phenyl]-1-piperazinecarboxylate

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Reaction Conditions

Reaction Steps

Under nitrogen, 3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amine (130 mg, 0.506 mmol) (Description 8) was dissolved in 1,4-dioxane (3 mL) and water (1 mL) and 1,1-dimethylethyl 4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1-piperazinecarboxylate (294 mg, 0.758 mmol), tetrakis(triphenylphosphine)palladium(0) (58.4 mg, 0.051 mmol) and potassium carbonate (210 mg, 1.517 mmol) were added. The mixture was then heated in a microwave at 120° C. for 30 min. Ethyl acetate (10 mL) was added and the mixture washed with water (2×5 mL). The organic layer was dried over MgSO4, filtered and solvent removed in vacuo. Purification by chromatography on silica gel, eluting with a gradient of 0-70% ethyl acetate in cyclohexane, afforded the title compound (197 mg). LCMS (A) m/z: 439 [M+1]+, Rt 0.99 min (acidic).

Provenance & Evidence