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6) δ 13.15 (1H, s), 8.52 (1H, d, J = 2.4 Hz), 8.45 (1H, dd, J = 3.9, 1.2 Hz), 8.34 (1H, dd, J = 9.0, 2.4 Hz), 7.94 (1H, dd, J = 4.8, 1.2 Hz), 7.48 (1H, d, J = 9.0 Hz), 7.28 (1H, dd, J = 5.1, 3.9 Hz). m/z = 274 (M+1).
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19
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36248970787
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This reaction proved to be particularly capricious. Careful control of temperature, concentration and the ratio of DMF: 1,2-DCE proved to be crucial for a successful outcome.
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20
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36248974294
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Other Suzuki couplings with 15 were performed using the following boronic acids or esters to give coupled products in 30-50% yield: phenyl, 3-furyl, 3-pyridyl, 4-pyridyl, 5-pyrimidyl, isoxazol-4-yl, 3,5-dimethyloxazol-4-yl and 1-methylpyrazol-4-yl. Reaction with imidazole-4-boronic acid resulted in hydrolysis of the starting material.
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27
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33748529352
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31
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36248988126
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note
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2, or ligand, was not performed. However, previous efforts to directly displace the chloro-group from compound 15 using either an alcohol or an alkoxide were unsuccessful.
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