1089333-87-8Relevant articles and documents
Bis/hetero aromatic compound and preparation method thereof
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Paragraph 0033-0034, (2021/07/17)
The invention discloses a bi/hetero aromatic compound and a preparation method thereof. The structural formula of the bi/hetero aromatic compound is as shown in formula 3. The preparation method comprises the following steps: taking an aryl tetrafluorobor
Synthesis method of canagliflozin
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Paragraph 0015, (2019/02/27)
The invention relates to a synthesis method of canagliflozin. According to the synthesis method, 4-fluorophenylboronic acid is taken as an initial raw material to be coupled with 2-methyl-5-bromo-thiophene to synthesize 2-methyl-5-(4-fluorophenyl)thiophene, the 2-methyl-5-(4-fluorophenyl)thiophene undergoes bromation and then undergoes Friedel-Crafts alkylation reaction with 4-bromotoluene to synthesize 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene, and the 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene undergoes condensation, etherification and methoxyl removal with 2,3,4,6-tetra-O-trimethylsilyl-D-gluconolactone to obtain the hypoglycemic drug canagliflozin. The synthesis method has the following advantages: compared with the conventional synthesis methods, the synthesisprocess takes the 4-fluorobenzeneboronic acid as an initial raw material, so that the raw material is cheap and easy to get, the process is easy to realize industrialization, the synthesis route is short and the operation is easy; in the synthesis process, bromine is not used or butyl lithium does not need to be used twice, so that the risk of the process can be reduced; in addition, the synthesis method is capable of improving the yield of canagliflozin products to 70% or more.
A C-H borylation approach to suzuki-miyaura coupling of typically unstable 2-heteroaryl and polyfluorophenyl boronates
Robbins, Daniel W.,Hartwig, John F.
supporting information; experimental part, p. 4266 - 4269 (2012/10/08)
A method for the synthesis of biaryls and heterobiaryls from arenes and haloarenes without the intermediacy of unstable boronic acids is described. Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ. They couple with aryl halides in the presence of simple palladium catalysts, providing a convenient route to biaryl and heteroaryl products that have been challenging to prepare via boronic acids.