3H-pyrrolopyridine compound or its N-oxide, or their salts and agricultural and horticultural pesticides containing the compound and methods of use thereof
A technology of pyrrolopyridine and compound, which is applied in the field of agricultural and horticultural pesticides and can solve problems such as undisclosed condensed heterocyclic compounds
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[0057] [Process a] production method
[0058] The compound represented by general formula (1) can be prepared from 1H-pyrrolopyridine compound (2) according to the method described in International Publication No. 2014 / 157600, according to the method described in the literature (Organic Letters, 13(17), 4498- 4501,2011) for preparation.
[0059] As the process can be used to introduce fluorine atoms as R 5 or R 6 Fluorinating reagents, such as N-fluoro-N'-(chloromethyl) triethylenediamine bis(tetrafluoroborate) (Selectfluor), (PhSO 2 ) 2 NF, N-fluoropyridine trifluoromethanesulfonate etc., preferably Selectfluor. The amount of the fluorinating agent used is usually 1 to 10 molar equivalents relative to 1 mole of compound (2).
[0060] This step is usually carried out in the presence of a base, and examples of usable bases include sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate, sodi...
reference example 1
[0251] The preparation method of reference example 1.1-trimethylsilyl-2-(2-ethylthio-4-trifluoromethylphenyl)acetylene
[0252] [chemical formula 7]
[0253]
[0254] Under argon, 2-ethylthio-4-trifluoromethyliodobenzene (3g), tetrahydrofuran (5ml), triethylamine (2ml), trimethylsilylacetylene (1.3g), bistri A mixture of phenylphosphinepalladium dichloride (315 mg), copper iodide (171 mg) and triphenylphosphine (118 mg) was heated and stirred at 40°C for 2 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was subjected to chromatography to obtain the target compound (3.2 g).
[0255] Physical properties: 1 H-NMR (CDCl 3 ): 7.92(d, 1H), 7.34(d, 1H), 7.07(dd, 1H), 2.99(dd, 2H), 1.42(t, 3H), 0.29(s, 9H)
reference example 2
[0257] Preparation method of 2-(2-ethylthio-4-trifluoromethylphenyl)-6-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine
[0258] [chemical formula 8]
[0259]
[0260] Under argon, p-1-trimethylsilyl-2-(2-ethylthio-4-trifluoromethylphenyl)acetylene (794 mg), 3-amino-2-chloro-5-trifluoro Picoline (650 mg, 1.1 equivalents), triethylamine (1 ml), diphenylphosphinoferrocenepalladium dichloride (141 mg), copper iodide (33 mg), DMF (5 ml) and 1M tetrabutyl fluoride A mixture of ammonium chloride in THF (tetrahydrofuran) (4 mL) was heated to reflux for 4 hours. The reaction solution was concentrated, and the resulting residue was chromatographed to obtain the target compound 2-(2-ethylthio-4-trifluoromethylphenyl)ethynyl-5-trifluoromethylpyridin-3-amine ( 0.54g). The obtained compound was dissolved in DMF (3 mL), and potassium tert-butoxide (672 mg, 3 equivalents) was added, followed by heating and stirring at 100° C. for 3 hours. After cooling to room temperature, silica gel was add...
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