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<example id="h0294" title="EXAMPLE 126"><heading id="h0295" title="5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide"><p id="p0413" num="0413">
<chemistry id="chem0202" num="0202"><img id="ib0202" file="imgb0202.tif" wi="72" he="33" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0414" num="0414">A slurry of the ester from example 113 step 1 (0.50g, 0.177 mmol) and 4-fluorobenzylamine (0.243g, 1.94 mmol) in toluene (2 mL) were heated at reflux for 20 hrs. Upon cooling to room temperature, the resulting solids were collected by filtration and washed with methanol (3ml) and then with diethyl ether (5ml) to afford the title compound as a white solid.<br/>
<spectrum type="hnmr">1H NMR (<quantity type="solvent">CDCl3</quantity>, <quantity type="frequency"><value><point>400</point></value><units>MHz</units></quantity>) δ <peaks type=".."><peak><quantity type="shift"><value><point>9.20</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>4.3</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.56</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>8.4</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.17</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak>, <peak><quantity type="shift"><value><point>7.74</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">dd</quantity>, J=<quantity type="coupling"><value><point>8.4</point></value> and <value><point>4.3</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.39</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak>, <peak><quantity type="shift"><value><point>7.07</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">t</quantity>, J=<quantity type="coupling"><value><point>8.6</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>4.67</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>6.2</point></value> <units>Hz</units></quantity>)</peak> ppm</peaks></spectrum>.<br/>
FAB MS calcd for BrC<sub>16</sub>H<sub>11</sub>N<sub>3</sub>O<sub>2</sub>F 376 (MH<sup>+</sup>), found 376.</p></heading></example>
