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US 11,739,066 B2Granted
Method for fluoroalkylation of enamines
AssigneeArxada AG
InventorsChristoph Taeschler, Matthias Beller, Helfried Neumann, Florian Fischer, Shaoke Zhang, Fei Ye, Stefan Ellinger, Florencio Zaragoza Doerwald
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Abstract
The invention discloses a method for fluoroalkylation of enamines with a fluoro alkyl halide in the presence of a base.
Claims18
A method for a fluoroalkylation of an enamine ENAM by a reaction REAC2, wherein
- ENAM is reacted with a fluoro alkyl halide FAHALIDE in the presence of a base BAS;
- wherein
- FAHALIDE is a compound of formula (FAHALIDE);
- X2-R3-X1 (FAHALIDE)
- R3 is C1-20 alkylene, wherein in the alkylene chain at least one of the hydrogens is substituted by F;
- X1 is Cl, Br or I;
- X2 is C(O)—OC1-4 alkyl, F, Br or H;
- BAS is selected from the group consisting of Na3PO4, Na2HPO4, K3PO4, K2HPO4, Na2CO3, NaHCO3, K2CO3, KHCO3, Cs2CO3, CsHCO3, NaOH, KOH, NaOtBu, KOtBu, and DBU;
- wherein the reaction REAC2 is performed in the absence of a metal catalyst, in the absence of a Pd catalyst;
- wherein the fluoroalkylation of said enamine ENAM by a reaction REAC2 occurs at a carbon atom of said ENAM;
- and
- wherein
- ENAM is a compound of formula (ENAM);
- wherein
- the N atom depicted with (i) is a tertiary, non-aromatic N atom;
- the C atoms depicted with (ii) and (iii) are non-aromatic C atoms;
- wherein the reaction is between about 16 hours and about 96 hours and the reaction temperature is between about 25° C. and about 80° C.;
- and
- wherein the reaction REAC2 excludes perfluoroalkyl iodide.
16 more elements
Dependencies are inferred from the claim text.