Sodium Carbonate → 3-Bromo-2-phenylthieno[2,3-c]pyridine

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Reaction Conditions

Reaction Steps

A mixture of 2,3-dibromothieno[2,3-c]pyridine (500 mg, 1.71 mmol), phenylboronic acid (197 mg, 1.61 mmol), Pd(PPh3)4 (187 mg, 0.16 mmol), 2.0 M aqueous sodium carbonate (4 mL, 8 mmol) in DME (25 mL) was evacuated and refilled with nitrogen 3× and then heated in a microwave at 100° C. for 30 min. The reaction was diluted with EtOAc and washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was dried over anhydrous sodium sulfate and purified by ISCO chromatography (0 to 25% EtOAc:heptane) to afford 162 mg (35%) of the title compound as a white solid. 1H NMR (acetone-d6): δ 9.24 (s, 1 H), 8.65 (d, J=5.5 Hz, 1 H), 7.82 (dd, J=7.9, 1.5 Hz, 2 H), 7.76 (d, J=5.5 Hz, 1 H), 7.55-7.61 (m, 3 H); MS (ESI): 290.36, 292.34 [M+H]+; HPLC tR=1.25 min (HPLC: Analytical—2 min).

Provenance & Evidence