반응 #476742

반응 방정식

2,3-dibromothieno[2,3-c]pyridine

phenylboronic acid

sodium carbonate

→

title compound

수율 35.0%

3-bromo-2-phenylthieno[2,3-c]pyridine

수율 35.0%

용매

DME

반응 조건

후처리

1. 1
   기타was evacuated
2. 2
   workup.ADDITIONrefilled with nitrogen 3×
3. 3
   workup.ADDITIONThe reaction was diluted with EtOAc
4. 4
   세척washed with saturated aqueous sodium bicarbonate, water and brine
5. 5
   건조The organic layer was dried over anhydrous sodium sulfate
6. 6
   기타purified by ISCO chromatography (0 to 25% EtOAc:heptane)

실험 절차

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).

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