Preparation and application of pyrazole oxime ester derivative having N-(3-chloropyridin-2-yl)pyrazole structure
A technology of ester derivatives and chloropyridine is applied in the field of preparation and application of pyrazole oxime ester derivatives to achieve the effect of excellent control effect
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Embodiment 1
[0031]
[0032]
[0033] Add 4mmol IIIa, 2mL triethylamine and 20mL acetonitrile into a 50mL round bottom flask. Under stirring in an ice bath, a mixed solution of 6 mmol of II and 2 mL of acetonitrile was slowly added dropwise thereto. After dropping, the mixture was stirred in an ice bath for 13 hours. The solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the target compound Ia; 1 H NMR (400MHz, CDCl 3 )δ: 8.47(d, J=3.6Hz, 1H, Py-H), 7.93(s, 1H, CH=N), 7.86(d, J=7.6Hz, 1H, Py-H), 7.56(s, 1H, Thiazole-H), 7.35~7.38(m, 1H, Py-H), 7.21~7.32(m, 2H, Ar-H), 7.10(s, 1H, Ar-H), 6.84(d, J= 8.0Hz,1H,Ar-H),6.45(s,1H,Pyrazole-H),5.41(s,2H,CH 2 ),3.60(s,3H,N-CH 3 ),2.44(s,3H,CH 3 ).
Embodiment 2
[0035]
[0036] In a 50 mL round bottom flask, add 3 mmol IIIb, 2 mL triethylamine and 25 mL dichloromethane. Under stirring in an ice bath, a mixed solution of 4 mmol of II and 2 mL of dichloromethane was slowly added dropwise thereto. After dropping, continue stirring in ice bath for 16 hours. The solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the target compound Ib; 1 H NMR (400MHz, CDCl 3 )δ: 8.39(d, J=4.0Hz, 1H, Py-H), 7.79(d, J=4.0Hz, 2H, Py-H and CH=N), 7.50(s, 1H, Thiazole-H), 7.28~7.31(m,1H,Py-H),6.69~7.13(m,4H,Ar-H),6.33(s,1H,Pyrazole-H),5.34(s,2H,CH 2 ),3.84(s,3H,OCH 3 ),3.57(s,3H,N-CH 3 ),2.34(s,3H,CH 3 ).
Embodiment 3
[0038]
[0039] In a 100 mL reaction flask, add 6 mmol IIIc, 2 mL of pyridine and 30 mL of DMF. Under stirring at room temperature, a mixture of 7 mmol of II and 4 mL of DMF was slowly added dropwise thereto. After dropping, the reaction was continued at room temperature for 15 hours. The solvent was evaporated under reduced pressure, and the residue was separated and purified by column chromatography to obtain the target compound Ic; 1 H NMR (400MHz, CDCl 3 )δ: 8.46(d, J=4.8Hz, 1H, Py-H), 7.85~7.87(m, 2H, Py-H and CH=N), 7.56(s, 1H, Thiazole-H), 7.40~7.42 (m,1H,Ar-H),7.34~7.37(m,1H,Py-H),6.72~7.26(m,3H,Ar-H),6.44(s,1H,Pyrazole-H),5.41(s ,2H,CH 2 ),3.61(s,3H,N-CH 3 ),2.45(s,3H,CH 3 ).
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