Arylpyrrole compound with biological activity and preparation method thereof
A technology for arylpyrrole compounds, which is applied in the field of arylpyrrole compounds and can solve the problem of high toxicity
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Embodiment 1
[0040] This example illustrates the preparation of compound 01.
[0041] Synthesis of 2-(4-chlorophenyl)-2-aminoacetic acid (α-p-chlorophenylglycine): 4-chlorobenzaldehyde (28.1g=0.20mol), ammonium bicarbonate (39.5g=0.50mol) , sodium cyanide (11.8g=0.24mol), ethanol (100ml) and water (100ml) after 75-80 ℃ of reaction 4-5hr, dropwise (10%, 180g=0.45mol) the aqueous solution of sodium hydroxide, and At the same time, the ethanol was removed, and then water (50-80ml) was added to react in an autoclave at 140-150°C for 4-5hr. After cooling, the solid was filtered off, the filtrate was adjusted to neutral with 10% hydrochloric acid, filtered, and dried to obtain 28.1 g of the title product as a white solid, yield 75.6%, melting point: 228-230°C. LC-MS (APCI, Neg) (M + -1)(relative intensity%): calc: 184, found: 184.0.
[0042] Synthesis of 2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile: 2-(4-chlorophenyl)-2-aminoacetic acid (α-p-chlorophenylglycine) (28.1 g=0.15mol...
Embodiment 2
[0046] This example illustrates the preparation of compound 02.
[0047] (R / S) Synthesis of 1-(2-chloro-1-ethoxyethyl)-4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile (02 compound):
[0048] To sodium hydride (60%, 0.48g=0.012mol) in anhydrous tetrahydrofuran (20ml) solution, add dropwise successively by 3.5g (0.01mol) 4-bromo-2-(4- A solution composed of chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile and 8ml of anhydrous tetrahydrofuran and 1.72g (0.012mol) of 1.2-dichloro-1-ethoxyethane, after dropping, reflux React overnight. After cooling, the reaction mixture was poured into ice water, extracted 2 times with ethyl acetate, the combined extracts were washed 2-3 times with water, anhydrous Na 2 SO 4 Dry and concentrate to obtain crude product. Column chromatography using a mixture of ethyl acetate and petroleum ether (1:50) as the eluent gave 2.2 g of the title compound as a white solid, content 95.0%, yield 45.7%, melting point: 167.3-169.5°C...
Embodiment 3
[0050] This example illustrates the preparation of compound 05.
[0051] Synthesis of 1-(3,3-dichloro-2-allyl)-4-bromo-2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile (compound 05):
[0052] To a solution composed of sodium ethoxide (1.1g=0.016mol) and anhydrous tetrahydrofuran (20ml), add 4-bromo-2-(4-chlorophenyl)-5-trifluoromethyl prepared by the method in Example 1 dropwise in sequence A solution composed of pyrrole-3-carbonitrile (3.50g=0.01mol) and anhydrous tetrahydrofuran (10ml) and 1,1,3-trichloro-2-propene (1.74g=0.012mol), after the dropwise, reflux reaction 6 -7hr. After cooling, the reaction mixture was poured into ice water, extracted 2 times with ethyl acetate, the combined extracts were washed 2-3 times with water, anhydrous Na 2 SO 4 Dry and concentrate to obtain crude product. Column chromatography was performed using a mixture of ethyl acetate and petroleum ether (1:50) as the eluent to obtain 2.42 g of the title compound as a yellow viscous l...
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