preparation and application of 2,3,6-trifluoropyridine_industrial additives

background and overview of preparation and application of 2,3,6-trifluoropyridine

2,3,6-trifluoropyridine is a chemical substance that is a transparent, polycarbonate-free liquid. 2,3,6-trifluoropyridine can be obtained from 2,3,5,6-tetrafluoropyridine by removing one fluorine. there are reports in the literature that 2,3,6-trifluoropyridine can be used to prepare small molecule inhibitors of malt1.

preparation and application of 2,3,6-trifluoropyridine

dissolve bdialh2 (29mg, 0.081mmol, 1 equivalent) in c6h6 (0.3ml) and [cp*rhcl (μ-cl)]₂ (1) (1mg, 0.0016mmol, 0.02 equivalent), suspend it in c6h6 (0.2ml), combine the mixture to obtain a light brown solution, add it to 2,3,5,6-tetrafluoropyridine (0.081mmol, 1 equivalent), and add α, α, α-trifluorotoluene (10.1 μl, 0.081 mmol, 1 equivalent) was used as an internal standard. the resulting solution was transferred to a j-young nmr tube equipped with a c6d6 capillary and sealed with a teflon cap. the nmr spectrum was measured to determine the fluoroarene the initial concentration. heat the nmr tube at 100 °c, quench the reaction by adding meoh (0.05 ml) to the nmr tube, and heat at 100 °c for 2 h to obtain the product 2,3,6-trifluoropyridine (29%), area selectivity: >99%, chemical selectivity: 89.4%, ton: 9.1, tof: 2.3-1, yield: 32.5%.

preparation and application of 2,3,6-trifluoropyridine

2,3,6-trifluoropyridine can be used as a pharmaceutical intermediate for the synthesis of the following pyrazole derivatives. this type of compound is a small molecule inhibitor of malt1. malt1 is a paracaspase-like enzyme related to proteases of the caspase (cysteine-aspartic acid protease) family, but it follows an arginine or lysine residue instead of cleavage occurs after aspartate (rebeaud et al., 2008). malt1-deficient animals display defects in b and t cell function but are otherwise healthy (ruefli-brasse et al., 2003; ruland et al., 2003), and malt1 is the only paracaspase in the human genome. these factors suggest that malt1-targeted therapy will likely be well tolerated and have few or manageable toxicities. therefore, malt1 represents a potentially important therapeutic target for abc-dlbcl and malt lymphoma.

references

[1] ekkert o, strudley s d a, rozenfeld a, et al. rhodium catalyzed, carbon–hydrogen bond directed hydrodefluorination of fluoroarenes[j]. organometallics, 2methoxypyridine014, 33(24):7027-7030 .

[2] from u.s. pat. appl. publ., 20190381019, 19 dec 2019