CN114507162A - 一种制备2-氟-5-甲氧基苯磺酰氯的方法 - Google Patents
一种制备2-氟-5-甲氧基苯磺酰氯的方法 Download PDFInfo
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
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- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C07C303/08—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with halogenosulfonic acids
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- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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Abstract
本发明公开了一种制备2‑氟‑5‑甲氧基苯磺酰氯的方法。该方法以对氟苯酚为原料，经溴代、磺化、甲醚化反应，再经还原脱溴和氯代反应制得2‑氟‑5‑甲氧基苯磺酰氯。本发明的方法，操作简单，反应条件相对温和，成本低，收率高，适合工业化生产。
Description
技术领域：
本发明属于药物化学领域，具体涉及一种制备2-氟-5-甲氧基苯磺酰氯的方 法。
背景技术：
2-氟-5-甲氧基苯磺酰氯(CAS号：1214334-01-6)，结构如式I所示，是合 成多种新药的重要中间体。
专利WO2014140065中公开一种新的化合物，N-(4-(氮杂吲哚-6-基)-苯基)- 磺酰胺是有价值的药理学活性的化合物，其调节蛋白激酶活性，特别是血清和 糖皮质激素调节激酶(SGK)的活性，是潜在的用于治疗SGK活性不适当疾病 的药物，例如退化性关节疾病或炎性过程诸如骨关节炎或风湿病。其中，N-[4-(3- 氨基-4-异丁氧基-1H-吡唑并[3,4-d]嘧啶-6-基)-苯基]-2-氟-5-甲氧基-苯磺酰胺； N-[4-(3-氨基-1H-吡唑并[3,4-d]嘧啶-6-基)-苯基]-2-氟-5-甲氧基-苯磺酰胺； N-{4-[4-(1-乙酰基-哌啶-4-基氧基)-3-甲基-1H-吡唑并[3,4-d]嘧啶-6-基]-苯基}-2- 氟-5-甲氧基-苯磺酰胺等都是由2-氟-5-甲氧基苯磺酰氯作为原料制备而来。
专利WO2015198045中公开新化合物3-取代的2-胺基吲哚衍生物及类似物， 其是潜在的治疗或预防与GPR43受体有关病症的药物，如糖尿病、肥胖症和炎 症性肠病。其中，2-氟-5-甲氧基苯磺酰氯是合成相关化合物的重要原料，合成 路线如Scheme 1所示。
目前，并无现有技术公开报道2-氟-5-甲氧基苯磺酰氯的制备方法。
发明内容：
本发明的目的在于针对现有技术的不足，提供一种操作简单易于产业化的 2-氟-5-甲氧基苯磺酰氯的制备方法。
本发明采用的技术方案如下：
具体步骤为：
步骤a)：以对氟苯酚为原料，经溴代反应生成化合物III；
步骤b)：化合物III经磺化反应制得化合物IV；
步骤c)：化合物IV经甲基化反应制得化合物V；
步骤d)：化合物V经还原脱溴反应制得化合物VI；
步骤e)：化合物VI经氯代反应制得2-氟-5-甲氧基苯磺酰氯；
进一步，步骤a)中所述溴代反应使用的试剂选自液溴、N-溴代丁二酰亚胺， 优选液溴。
进一步，步骤b)中所述磺化反应使用的试剂选自氯磺酸、硫酸、发烟硫酸、 三氧化硫，优选氯磺酸。
进一步，步骤c)中所述甲基化反应使用的试剂选自三氟甲磺酸甲酯、对甲 苯磺酸甲酯、硫酸二甲酯，优选三氟甲磺酸甲酯。
进一步，步骤d)中所述还原脱溴反应可以选用Pd/C催化剂，镍催化，优选 Pd/C催化剂。
进一步，步骤e)中所述氯代反应使用的试剂选自三氯氧磷、三氯化磷、五 氯化磷、浓盐酸和无水氯化锌的混合物、二氯亚砜、磺酰氯，优选二氯亚砜。
本发明的有益效果在于，本发明公开了一种以对氟苯酚为原料，制备2-氟-5- 甲氧基苯磺酰氯的方法，操作简单，反应条件相对温和，成本低，收率高，适 合工业化生产。
附图说明
图1实施例5中得到的2-氟-5-甲氧基苯磺酰氯的1HNMR图
具体实施方式
下面结合具体实施例对本发明的技术内容作进一步的阐述，其目的是为了 更好的理解本发明的内容，但本发明的保护范围不限于此。
实施例1化合物III的制备
室温下，25mL三口瓶中加入2.0g对氟苯酚，18mL乙酸，向其中滴加5.99 g液溴，搅拌1小时反应结束，再向其中加入冰水，有固体析出，过滤，滤饼加 6mL水洗，滤饼室温敞口晾干得到3.76g黄色固体，即为化合物III。
实施例2化合物IV的制备
将实施例1中得到的化合物III滴加进冰水中搅拌，保持温度小于10℃时 滴加氢氧化钠水溶液(13.34g溶于20mL水)，再加入10mL四氢呋喃，升温 至40℃搅拌4小时，反应结束，静止分层，将有机层减压浓缩，得到1.76g化 合物IV。
实施例3化合物V的制备
在25mL三口瓶中加入2.0g实施例2中得到的化合物IV，8mL DMF，1.58 g碳酸钾，再向其中滴加1.88g三氟甲磺酸甲酯，在25℃反应2小时，反应结 束，萃取分层，合并有机相旋蒸干得化合物V。
实施例4化合物VI的制备
在100mL单口瓶中，加入2g实施例3中得到的化合物V、2.27g氢氧化 钾，0.2g钯碳和10mL水，抽真空后通入氢气，室温反应4小时。反应完毕， 抽滤，减压蒸干，用少量丙酮打浆，抽滤，真空干燥得到化合物VI。
实施例5化合物I的制备
25mL三口瓶中加入2.0g实施例4中得到的化合物VI，加入5mL二氯亚 砜，1滴DMF，回流搅拌4小时，反应结束，旋转蒸干二氯亚砜得到产品2-氟 -5-甲氧基苯磺酰氯，1HNMR图谱见图1。
Claims (6)
1.一种制备2-氟-5-甲氧基苯磺酰氯的方法，其特征在于，所述方法包括如下步骤：
步骤a)：以对氟苯酚为原料，经溴代反应生成化合物III；
步骤b)：化合物III经磺化反应制得化合物IV；
步骤c)：化合物IV经甲醚化反应制得化合物V；
步骤d)：化合物V经还原脱溴反应制得化合物VI；
步骤e)：化合物VI经氯代反应制得2-氟-5-甲氧基苯磺酰氯；
具体路线如下所示：
2.一种如权利要求1所述的制备方法，其特征在于，步骤a)中所述的溴代反应所用的试剂选自液溴、N-溴代丁二酰亚胺。
3.一种如权利要求1所述的制备方法，其特征在于，步骤b)中所述磺化反应所用的试剂选自氯磺酸、硫酸、发烟硫酸、三氧化硫。
4.一种如权利要求1所述的制备方法，其特征在于，步骤c)中所述甲醚化反应的试剂选自三氟甲磺酸甲酯、对甲苯磺酸甲酯、硫酸二甲酯。
5.一种如权利要求1所述的制备方法，其特征在于，步骤d)中所述还原脱溴反应可以选用Pd/C催化剂、镍催化剂。
6.一种如权利要求1所述的制备方法，其特征在于，步骤e)中所述氯代反应的试剂选自三氯氧磷、三氯化磷、五氯化磷、二氯亚砜、磺酰氯。
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| CN1234033A (zh) * | 1996-08-27 | 1999-11-03 | 美国家用产品公司 | 作为多巴胺d2激动剂的4－氨基乙氧基－吲哚衍生物 |
| US6211223B1 (en) * | 1997-10-22 | 2001-04-03 | Pfizer Inc. | Indole derivatives useful in therapy |
| CN103012407A (zh) * | 2011-09-27 | 2013-04-03 | 赛诺菲 | N-[4-(1H-吡唑并[3,4-b]吡嗪-6-基)-苯基]-磺酰胺类及其作为药物的用途 |
| CN108368104A (zh) * | 2015-10-15 | 2018-08-03 | 伊文蒂瓦公司 | Yap/taz-tead相互作用的新化合物抑制剂及其在治疗恶性间皮瘤中的用途 |
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| CN1234024A (zh) * | 1996-08-27 | 1999-11-03 | 美国家用产品公司 | 4－氨基乙氧基吲哚衍生物 |
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