Examples of uses of 1-fluoro-2,4,6-trimethylpyridine trifluoromethanesulfonate_Industrial additives

Background and overview of examples of uses of 1-fluoro-2,4,6-trimethylpyridine trifluoromethanesulfonate

1-Fluoro-2,4,6-trimethylpyridine trifluoromethanesulfonate is a fluorination reagent that can be used in electrophilic fluorination reactions. There are reports in the literature that it can be used to prepare favipiravir.

Examples of uses and applications of 1-fluoro-2,4,6-trimethylpyridine trifluoromethanesulfonate

Examples of uses and applications of 1-fluoro-2,4,6-trimethylpyridine trifluoromethanesulfonate 1.

CN202010583503.1 reported that 1-fluoro-2,4,6-trimethylpyridine trifluoromethanesulfonate can be useful for preparing favipiravir and its derivatives. Specifically, compound A is used as the raw material, and a fluorine atom is selectively introduced at the 6-position through an electrophilic fluorination reaction to efficiently synthesize favipiravir or its derivatives, namely compound B, in one step. The general reaction formula is as follows:

Where R1 is -CONH2, -CONH2, -CONR3, -COOR3, one of the cyano groups. Benzylpyridine wherein R2 and R3 are H, C1-C6 alkyl, C1-C6 cycloalkyl, aryl-substituted alkyl. The above-mentioned one-step reaction refers to: placing compound A and fluorination reagent in a reaction solvent, and performing an electrophilic fluorination reaction at a certain temperature. The reaction temperature is 30-150°C, preferably 70-100°C. According to the above preparation method, the fluorinating reagent used in the electrophilic fluorination reaction includes but is not limited to N-F reagent. Specifically, it includes: the fluorinating reagent used in the electrophilic fluorination reaction is selected from: N-fluorobenzene Sulfonimide (NFSI), fluorobis(phenylsulfonyl)methane, N-fluoro-N-[4-(trifluoromethyl)phenyl]-(NFSA), 1-fluoro-4-hydroxy-1, 4-diazabicyclo[2.2.2]octane bistetrafluoroborate (Accnfluor), 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis( Tetrafluoroborate) salt (Selectfluor), N-fluoropyridinium (tetrafluoroborate or triflate), 1-fluoro-2,4,6-trimethylpyridine trifluoromethanesulfonate, etc. .

Examples of uses and applications of 1-fluoro-2,4,6-trimethylpyridine trifluoromethanesulfonate 2.

CN201610173119.8 reports an efficient synthesis method of 3-fluoro-fluorophenylboronic acid indole-2-carbonyl compound, including: in the presence of fluorinated reagents, solvents and additives, 3-hydrogen- Indole-2-ol compounds undergo fluorooxidation reaction to obtain the corresponding 3-fluoro-indole-2-carbonyl compound. The fluorinated reagent is 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octanebis(tetrafluoroborate) salt (fluorinated reagent), N-fluorobenzenesulfonate Amide, 1-fluoro-2,4,6-trimethylpyridine trifluoromethanesulfonate, 1-fluoro-4-methyl-1,4-diazabicyclo[2.2.2]octane bis(tetrakis) Fluoboric acid) salts of one or a mixture of several.

References

[1] [Chinese invention] CN202010583503.1 Preparation method of favipiravir and its derivatives

[2] [China invention, China invention authorization] CN201610173119.8 Efficient preparation method of 3-fluoro-indole-2-carbonyl compound