1,2-Dimethoxyethane → Ethyl 4-amino-3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 4-amino-2-bromo-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate (260 mg, 0.790 mmol) (Description 31), tetrakis(triphenylphosphine)palladium(0) (45.6 mg, 0.039 mmol), sodium carbonate (167 mg, 1.580 mmol) and 3-pyridineboronic acid (116 mg, 0.948 mmol) in acetonitrile (3 mL) and water (0.75 μl) was heated at 70° C. under nitrogen, for 30 min. 1,2-Dimethoxyethane (2 mL) was added and the mixture was stirred at 80° C. for 18 h. The reaction mixture was cooled to RT and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in DCM, afforded the title compound (141 mg). LCMS (A) m/z: 328 [M+1]+, Rt 0.88 min (acidic), Rt 1.14 min (basic).

Provenance & Evidence