37669-64-0 3-溴吡啶-5-甲醇

危险性质：非危险化学品

化学合成，医药中间体。

医药

合成路线 1（1. 合成：37669-64-0）

产率：95% 合成条件：With sodium tetrahydroborate In methanol at 0℃; for 1 h; 实验步骤：在0℃下，将硼氢化钠（2.2g，59.1mmol）加入到5-溴 - 吡啶-3-甲醛（10.0g，53.7mmol）的MeOH（100mL）悬浮液中。 将混合物在0℃下搅拌1小时，然后通过加入水（5.0mL）淬灭。 蒸发溶剂，得到浅黄色油状物，将其重新溶解在EtOAc中并用水洗涤。 用无水物干燥有机层。 过滤并真空浓缩Na 2 SO 4，得到标题化合物（9.6g，95％），为无色油状物。 MS：188.0和190.0（M + H +）。 参考文献：

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合成路线 2（2. 合成：37669-64-0）

产率：75% 合成条件：Stage #1: With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at -10℃; for 0.33 h; Inert atmosphere Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at -70 - 20℃; for 13.50 h; 实验步骤：19.1（5-溴吡啶-3-基）甲醇在氩气下，在-10℃下，加入12g（59.4mmol）5-溴吡啶-3-羧酸在300mL无水THF中的溶液，6.6 在-10℃下搅拌20分钟后，分批加入6mL NMM，然后5.7mL（59.4mmol）氯甲酸乙酯。分批加入6.8g（179.8mmol）硼氢化钠。然后将介质冷却至-70℃。 在1小时30分钟内加入400mL MeOH。然后使温度升至室温并继续搅拌12小时。然后在减压下浓缩该介质，然后在二氧化硅柱上通过色谱法纯化。 凝胶，用98/2 DCM / MeOH混合物洗脱。得到0.8g黄色油形式的（5-溴吡啶-3-基）甲醇。产率= 75％1 H NMR，CDCl 3,400MHz，δ（ppm） ：8.5（s，1H）; 8.4（s，1H）; 7.9（s，1H）; 4.6（s，2H）; 2.8（bs，1H） 参考文献：

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合成路线 3（3. 合成：37669-64-0）

产率：60% 合成条件：Stage #1: With sodium tetrahydroborate In methanol at 0℃; for 0.50 h; Stage #2: With water In methanol 实验步骤：（5-溴吡啶-3-基）甲醇。 向冷（0℃）的5-溴烟酸乙酯（1.0g，4.3mmol）的MeOH（15mL）溶液中分批加入硼氢化钠（650mg，17mmol）。 30分钟后 通过加入水（10mL）淬灭反应。 然后用二氯甲烷（3x）萃取反应。 合并萃取物，干燥（MgSO 4），浓缩滤液，通过硅胶柱色谱法（0至80％乙酸乙酯/己烷）纯化，得到475mg（60％）透明油状物。 1H-NMR（CDCl3,400MHz）δ8.57（s，1H），8.49（s，1H），7.91（s，1H），4.73（s，2H），2.51（s，br，1H）。 质谱：188.12（MH）+。 参考文献：

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