Preparation method of erlotinib intermediate, i.e., 3-aminobenzeneacetylene

Abstract

The invention discloses a preparation method of an erlotinib intermediate, i.e., 3-aminobenzeneacetylene. The method comprises the following steps of: performing a Vilsmeier reaction on 3-nitrobenzene ethyl ketone (I) serving as an industrial raw material to obtain an intermediate, i.e., 1-chloro-1-(3-nitrobenzophenone)-2-(N,N-dimethyl formaldehyde oxime)-yl-ethylene (II) containing a halogen-substituted alkene bond; performing a dehydration reaction to obtain a formyl intermediate, i.e., 1-chloro-1-(3-nitrobenzophenone)-2-formaldehyde)-yl-ethylene (III); performing an elimination reaction to obtain an intermediate, i.e., 3-nitrophenylacetylene (IV); and performing a nitro reduction reaction on the intermediate, i.e., 3-nitrophenylacetylene (IV) to obtain the erlotinib intermediate, i.e., 3-aminobenzeneacetylene (intermediate A). The preparation method can contribute to improving the atom economy, process simplicity and environment friendliness, so that the the erlotinib intermediate, i.e., 3-aminobenzeneacetylene can be prepared easily and conveniently.

Description

technical field [0001] The invention relates to a preparation method of an erlotinib intermediate, in particular to a preparation method of the erlotinib intermediate 3-aminophenylacetylene. Background technique [0002] Erlotinib (Erlotinib) is a new antagonist of epidermal growth factor receptor-tyrosine kinase (EGFR-TK), which was approved by the US Food and Drug Administration (FDA) and the European Medicines Agency ( EMEA) approval in the United States and EU countries, as a second-line or third-line drug for the treatment of patients with advanced or non-small cell lung cancer (NSCLC) who have failed other treatment options. The US Food and Drug Administration also approved it for the treatment of pancreatic cancer on September 13, 2005. It is now listed in seventy to eighty countries around the world. In 2007, the State Food and Drug Administration (SFDA) approved the listing of Erlotinib Hydrochloride preparations in my country. [0003] The medicinal active ingre...

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Problems solved by technology

[0018] It has been seen from the aforementioned background information that in the current method for preparing 3-aminophenylacetylene (intermediate A), either an expensive catalyst is used, or a C-C coupling reaction with a low yield is required, or a multi-step functional group Transformation can be made

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