* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] European Journal of Medicinal Chemistry, 1995, vol. 30, # 11, p. 839 - 850
[2] Patent: WO2005/102998, 2005, A1, . Location in patent: Page/Page column 32
2
[ 1313396-19-8 ]
[ 173850-41-4 ]
Yield
Reaction Conditions
Operation in experiment
59%
With silver tetrafluoroborate; phenol In tetrahydrofuran for 7 h; Reflux
General procedure: To a solution of alkynyl oxime ether 1 (0.15 mmol) in THF (5 mL) were added phenol (28 mg, 0.3 mmol) and AgBF4 (5.8 mg, 0.03 mmol), with a drying tube filled with silica gel at room temperature. After being stirred at reflux for 1-12 h (TLC monitoring), the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/AcOEt=3-10:1) to afford isoxazole 3. The physical and spectroscopic data of 3a5 and 3j12h were in accord with those reported in the literature.
With lithium aluminium tetrahydride; In diethyl ether; at 0 - 20℃; for 4h;Heating / reflux;
The product obtained in the previous step (0.450 g, 3.19 mmol) in diethyl ether was added dropwise to a suspension of lithium aluminiumhydride (0.121 g, 3.2 mmol) in diethyl ether (5.5 ml) at 0C. After stirring at room temperature and reflux temperature for 4 h, the reaction mixture was quenched with a saturated aqueous solution of sodium sulfate and filtered over dicalite. The filtrate was concentrated under reduced pressure to give a mixture of starting material and product. The procedure described above was repeated to complete the reaction, to give isoxazol-5-yl-methanol (0.300 g).
Isoxazole-5-carboxylic acid (0.500 g, 4.4 mmol) was dissolved in a solution of hydrochloric acid in ethanol (5 M) and refluxed for 5 hours. The mixture was concentrated under reduced pressure giving <strong>[21169-71-1]isoxazole-5-carboxylic acid</strong> ethyl ester, which was used immediately in the following step.
With n-butyllithium; triethylamine; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
2-Amino-4-isoxazol-5-yl-6-methylsulfanyl-pyrimidine-5-carbonitrile From <strong>[173850-41-4]isoxazole-5-carboxylic acid ethyl ester</strong> with acetonitrile and butyllithium in THF. Then treatment with sodium hydride, carbon disulphide and methyl iodide in DMSO. Then treatment with guanidine nitrate and triethylamine in DMF. EI-MS m/e (%): 233 (M+, 45), 206 ([M-HCN]+, 100), 151 (33).
With silver tetrafluoroborate; phenol; In tetrahydrofuran; for 7.0h;Reflux;
General procedure: To a solution of alkynyl oxime ether 1 (0.15 mmol) in THF (5 mL) were added phenol (28 mg, 0.3 mmol) and AgBF4 (5.8 mg, 0.03 mmol), with a drying tube filled with silica gel at room temperature. After being stirred at reflux for 1-12 h (TLC monitoring), the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/AcOEt=3-10:1) to afford isoxazole 3. The physical and spectroscopic data of 3a5 and 3j12h were in accord with those reported in the literature.
With [RuCl2pentamethylcyclopentadiene]n; silver trifluoroacetate; trifluoroacetic acid In 2,2,2-trifluoroethanol at 80℃; for 8h;
48 Example 48
The preparation method of compound I-24,Including the following process: 0.2mmol of 2-aminobenzaldehyde,Ethyl isoxazole-5-carboxylate 0.3mmol,Dichloro (pentamethylcyclopentadienyl) ruthenium () 0.005mmol,Silver trifluoroacetate 0.02mmol,Add 0.2mmol trifluoroacetic acid to the reaction tube,Dissolved in an appropriate amount of trifluoroethanol solvent,React at 80 for 8 hours,The reaction solution was filtered through diatomaceous earth, and the filtrate was concentrated,Purification by column chromatography gave 37.8 mg of the target product with a yield of 83%.
83%
With bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]; silver trifluoroacetate; trifluoroacetic acid In 2,2,2-trifluoroethanol at 80℃; for 10h;
2. Typical Catalytic Procedure
General procedure: A reaction tube (15 mL) equipped with a magnetic stirrer bar was charged with 2-aminobenzaldehyde 1a (0.1 mmol), isoxazole 2a (0.12 mmol), [Cp*RuCl2]2 (2.5 mol %), CF3COOAg (10 mol %), CF3COOH (1 equiv.) in anhydrous CF3CH2OH (1.5 mL). The reaction mixture was stirred at 80 for 10 h under air atmosphere. When the reaction was completed, the mixture was cooled to room temperature and then purified by column chromatography on silica gel with ethyl acetate/petroleum ether (1:5) to give the desired product 3a.
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