Kilogram-scale highly selective catalytic hydrogenation of the aryl nitro group in the intermediate of crizotinib has been developed, which adopted continuous-flow technology with prepassivated Raney Ni as a catalyst at room temperature. According to the reaction condition optimization, side reactions such as dehalogenation, debenzylation, and reduction of other unsaturated functional groups were inhibited eminently. Moreover, catalytic hydrogenation of (R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine (compound I) afforded the desired product (R)-3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]pyridin-2-amine (compound II) with high selectivity (99.9%) and high conversion (99.5%). Finally, high-quality crizotinib was synthesized from intermediate II.

中文翻译：

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连续流动中高效催化加氢合成克唑替尼中间体

克唑替尼中间体中芳基硝基的公斤级高选择性催化加氢反应已经开发出来，该反应采用连续流技术，在室温下采用预钝化阮内镍作为催化剂。根据反应条件的优化，显着抑制了脱卤，脱苄基和其他不饱和官能团还原等副反应。此外，（R）-3-（1-（2,6-二氯-3-氟苯基）乙氧基）-2-硝基吡啶（化合物I）的催化加氢得到所需产物（R）-3- [1-（2 ，6-二氯-3-氟苯基）乙氧基]吡啶-2-胺（化合物II），具有高选择性（99.9％）和高转化率（99.5％）。最后，从中间体II合成了高质量的crizotinib 。