1225916-69-7

Upstream product

• 127-08-2 potassium acetate 
• 636-72-6 2-thiophenemethanol 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 1765-93-1 4-fluoroboronic acid 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 

Downstream Products

• 1355034-72-8 C₁₁H₈FN₃S 
• 1355034-97-7 C₂₇H₂₈FN₃O₉S 
• 1355034-98-8 C₁₉H₂₀FN₃O₅S 
• 1358581-37-9 (2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 1030825-20-7 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl bromide 
• 842133-18-0 canagliflozin 

Relevant academic research and scientific papers

Preparation method of canagliflozin

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 5-bromo-thiophene-2-formaldehyde to synthesize 5-(4-fluorophenyl)thiophene-2-formaldehyde, the 5-(4-fluorophenyl)thiophene-2-formaldehyde undergoes reduction and chlorination 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, etherificationand methoxyl removal with 2,3,4,6-tetra-O-trimethylsilyl-D-gluconolactone to obtain the hypoglycemic drug canagliflozin. The preparation method has the following advantages: compared with the conventional preparation methods, the synthesis process 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 preparation method is capable of improving the yield of canagliflozin products to 70% or more.

Facile synthesis of 1,2,3-triazole analogs of SGLT2 inhibitors by 'click chemistry'

Novel analogs of SGLT2 inhibitors containing the 1,2,3-triazole motif were designed and synthesized for urinary glucose excretion evaluation. The C-glucosides with triazole aglycone can be easily constructed by click chemistry. Most of the synthesized compounds increased urinary glucose excretion and demonstrated inhibition of glucose transport.

Palladium-catalysed direct arylation of heteroaromatics bearing unprotected hydroxyalkyl functions using aryl bromides

Heteroaromatics bearing unprotected hydroxyalkyl functions can be arylated using aryl or heteroaryl bromides, via palladium-catalysed carbonhydrogen bond activation/arylation. Good yields were generally obtained using 0.01-0.5 mol% of the air-stable palladium acetate complex as the catalyst. The nature of the base was found to be crucial for the selectivity of this reaction. Potassium acetate led to the direct arylation products whereas caesium car-bonate led to the formation of the ether. This procedure is certainly more atom-economic than other methods for the preparation of such compounds, as no protection/ deprotection sequence of the hydroxyalkyl function and no preparation of an organometallic derivative is required.