Method for preparation of 6-trifluoromethylpyridine-3-carboxylic acid derivatives from trifluoroacetylacetic acid
a trifluoroacetylated acid and derivative technology, applied in the field of trifluoroacetylated enamine derivatives, can solve the problems of trifluoroacetylated enamin
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example 1
Reaction (ReacS1)
[0101]A mixture of compound of formula (II-2) (0.10 g, 0.64 mmol), DMF (0.5 ml), compound of formula (IV-1) (74 mg, 0.64 mmol), compound of formula (III-1) (0.16 ml, 0.96 mmol),
and sulfuric acid (0.007 ml, 0.13 mmol) was stirred at 80° C. for 3 h. A sample of the reaction mixture was diluted with brine (3 ml) and aqueous hydrochloric acid (1 N, 2 ml), and extracted with ethyl acetate (3 ml). After concentration under reduced pressure of the extract the analysis by 1H NMR showed compound of formula (I-1).
[0102]1H NMR (400 MHz, d6-DMSO): delta 2.78 (s, 3H), 3.91 (s, 3H), 7.89 (d, J=8 Hz, 1H), 8.44 (d, J=8 Hz, 1H).
example 2
Reaction (ReacS1)
[0103]A mixture of compound of formula (II-2) (0.12 g, 0.77 mmol), toluene (0.5 ml), compound of formula (IV-1) (113 mg, 0.98 mmol), compound of formula (III-1) (0.16 ml, 0.96 mmol), and trifluoroacetic acid (0.01 ml, 0.13 mmol) was stirred at 80° C. for 17 h. A sample of the reaction mixture was diluted with brine (3 ml) and aqueous hydrochloric acid (1 N, 2 ml), and extracted with ethyl acetate (3 ml). After concentration of the extract under reduced pressure the analysis by 1H NMR showed compound of formula (I-1), 1H NMR data was as shown in example 1.
example 3
Reaction (ReacS1)
[0104]A mixture of compound of formula (II-2) (0.169 g, 1.08 mmol), toluene (0.52 ml), compound of formula (IV-2) (0.26 mmol, prepared in analogy to example P2 of WO 2004 / 078729 A1, wherein the reaction mixture, which is obtained after cooling and which contains 3-amino-4-methoxyethoxy-but-2-enoic acid ethyl ester, which is compound of formula (IV-2), is taken and concentrated under reduced pressure, the thus obtained residue was used in instant example, the content of compound of formula (IV-2) in this residue is determined by 1H-NMR against a standard),
compound of formula (III-1) (0.40 ml, 2.4 mmol), and trifluoroacetic acid (0.01 ml, 0.13 mmol) was stirred at 80° C. for 18 h. The mixture was diluted with aqueous hydrochloric acid (1 N, 10 ml), extracted with ethyl acetate (1 time with 5 ml, 2 times with 2.5 ml), the combined extracts were washed with brine (5 ml), dried (MgSO4), and concentrated under reduced pressure, to yield the compound of formula (I-2) as an...
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