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Production method for fluorinated pyrazole derivative and intermediate thereof

A manufacturing method and compound technology, applied in the direction of organic chemistry method, hydrazone preparation, organic chemistry, etc.

Active Publication Date: 2020-12-25
KUMIAI CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the acrylic acid derivative specifically disclosed in Japanese Patent Laid-Open No. 6-166666 (Patent Document 2) is an unsubstituted acrylate

Method used

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  • Production method for fluorinated pyrazole derivative and intermediate thereof
  • Production method for fluorinated pyrazole derivative and intermediate thereof
  • Production method for fluorinated pyrazole derivative and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0673] (Process (pre-i))

[0674] Using ligand Ad 2 Production of 4,4,4-trifluoropropyl crotonate (A-E-a) of PBu

[0675] For example, the compound of formula (A) used as the raw material of step (i) can be produced as shown in the following scheme.

[0676] [chem 67]

[0677]

[0678] (E)-1-chloro-3,3,3-trifluoropropene (1-E-a) (0.65 g, 5 mmol, 100 mol%) as a starting compound, and palladium acetate (hereinafter sometimes abbreviated as Pd ( OAc) 2 ) (11mg, 0.05mmol, 1mol%) and Ad 2 PBu (36mg, 0.1mmol, 2mol%), 2-propanol (3.8mL, specific gravity: 0.79, 50mmol, 1000mol%) as alcohol, and triethylamine (1.4mL, specific gravity: 0.73, 10mmol, 200mol%) as base ) was housed in a stainless steel pressure vessel (autoclave). Fill the autoclave with carbon monoxide to 10kgf / cm 2 (160mol%), stirred at 100°C for 4 days.

[0679] After the reaction, the autoclave was ice-cooled to release the residual pressure. Trifluorotoluene (C 6 h 5 CF 3 , 0.37g, 2.5mmol, 50mol%) was a...

Embodiment 2～20

[0684] (Research on ligands in process (pre-i))

[0685] Production of Propyl 4,4,4-Trifluorocrotacrylate (A-E-a)

[0686] The reaction was carried out in the same manner as in Example 1 except that the ligand was changed as shown in Table 1 below. Among them, in order to study the influence due to the difference of the ligand, the reaction was stopped at 18 hours.

[0687] The reaction scheme is shown below.

[0688] [chem 68]

[0689]

[0690] Ligands used in Examples, related ligands and their abbreviations are shown below.

[0691] [chem 69]

[0692]

[0693] [chem 70]

[0694]

[0695] [chem 71]

[0696]

[0697] [chem 72]

[0698]

[0699] [chem 73]

[0700]

[0701] [chem 74]

[0702]

[0703] By using benzotrifluoride as an internal standard in the same manner as above 19 The obtained reaction mixture was analyzed by F NMR to determine the yield.

[0704] List the results in Table 1.

[0705] [Table 1]

[0706]

[0707]

[0708] ...

Embodiment 21～35

[0710] (The ligand Ad is used in the process (pre-i) 2 Study on the reaction conditions of PBu)

[0711] Production of Propyl 4,4,4-Trifluorocrotacrylate (A-E-a)

[0712] Using a particularly preferred ligand Ad 2 PBu, study reaction conditions.

[0713] In addition to changing the filling pressure of carbon monoxide, reaction temperature and ligand Ad as shown in Table 2 below 2 Except the amount of PBu, it reacted similarly to Example 1. Among them, in order to study the influence due to the difference of reaction conditions, 0.1mol% Pd(OAc) was used relative to the starting compound (1-E-a) 2 , the reaction was stopped at 18 hours.

[0714] The reaction scheme is shown below.

[0715] [chem 75]

[0716]

[0717] By using benzotrifluoride as an internal standard in the same manner as above 19 The obtained reaction mixture was analyzed by F NMR to determine the yield.

[0718] List the results in Table 2.

[0719] [Table 2]

[0720]

[0721] It was confirmed ...

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PUM

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Abstract

This method comprises steps: (i) reacting a compound represented by formula (A) with hydrazine to produce a compound represented by formula (B); (ii) reacting the compound represented by formula (B) with formaldehyde to produce a compound represented by formula (C); and (iii) reacting a compound represented by formula (C) in the presence of a base to produce a compound represented by formula (D).Here, Rf represents a (C1-C4) perfluoroalkyl, and R represents a (C1-C6) alkyl.

Description

technical field [0001] The present invention relates to a compound of the following formula (D), that is, a method for producing a fluorine-containing pyrazole derivative and an intermediate thereof. [0002] [chemical 1] [0003] [0004] (Here, Rf is (C1-C4) perfluoroalkyl). Background technique [0005] Pyrazole derivatives are well known as intermediates for the production of pharmaceuticals and agricultural chemicals (see, for example, WO2005 / 105755A1, WO2005 / 095352A1 and WO2004 / 013106A1). In Japanese Patent Application Laid-Open No. 2007-031342 (Patent Document 1), as a method for producing 5-hydroxy-1-alkylpyrazole derivatives, it is proposed to combine a β-ketoester compound having an electron-withdrawing group with an alkylhydrazine. A method of reacting under acidic conditions. However, the raw materials used in JP 2007-031342 (Patent Document 1) are expensive. In addition, from the viewpoint of throughput, there may be a relatively large problem in the avai...

Claims

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Application Information

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IPC IPC(8): C07D231/20C07C251/74C07B61/00C07C249/16
CPCC07B61/00C07C249/16C07C251/74C07D231/20
Inventor 有末芳
Owner KUMIAI CHEM IND CO LTD
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