Method for producing pyrazole derivative
View Patent ↗The invention relates to a production method of pyrazole derivative (6) by reacting compound (5) with an oxidant. wherein R 1 , R 2 , R 3 , X 1 , X 2 and Z 1 are as defined herein.
1. A compound represented by formula (5a)
wherein
R 12 is a methyl group or an ethyl group,
R 13 is a hydrogen atom, a methyl group or an ethyl group, and
X 11 and X 12 are each independently a fluorine atom or a chlorine atom.
2. A method of producing a compound represented by formula (5)
which comprises
reacting a compound represented by formula (1)
with a compound represented by formula (2)
to obtain a compound represented by formula (3)
and
reacting the compound represented by the formula (3) with a compound represented by formula (4a)
R 3 —NHNH 2 (4a)
to obtain a compound represented by formula (5),
wherein
R 1 is a hydrogen atom or a halogen atom,
R 2 is a C 1-8 alkyl group,
R 3 is a hydrogen atom or a C 1-8 alkyl group,
X 1 and X 2 are each independently a fluorine atom or a chlorine atom,
Z 1 is a hydrogen atom or a C 1-8 alkyl group,
R A is NR 5 R 6 , and R 5 and R 6 are each independently a C 1-8 alkyl group,
Y 1 is an oxygen atom,
X 3 is a halogen atom, and
the wavy lines mean that the configuration of Z 1 and R A relating to the double bond is E or Z.
3. A method of producing a compound represented by formula (5-1)
which comprises
reacting 1,1,2,2-tetrafluoro-N,N-dimethylethanamine with BF 3 to obtain a compound represented by formula (1b-1)
reacting the compound represented by formula (1b-1) with a compound represented by formula (2b-1)
to obtain a compound represented by formula (3a-1)
and
reacting the compound represented by formula (3a-1) with methylhydrazine to obtain a compound represented by (5-1).
4. A method of producing a pyrazole derivative represented by formula (6)
which comprises reacting a compound represented by formula (5)
with an oxidant
wherein
R 1 is a hydrogen atom or a halogen atom,
R 2 is a C 1-8 alkyl group,
R 3 is a hydrogen atom or a C 1-8 alkyl group,
X 1 and X 2 are each independently a fluorine atom or a chlorine atom, and
Z 1 is a hydrogen atom or a C 1-8 alkyl group.
5. The compound of claim 1 , wherein R 12 is a methyl group.
6. The compound of claim 1 , wherein R 13 is a methyl group.
7. The compound of claim 1 , wherein each of R 12 and R 13 is a methyl group.
8. The compound of claim 1 , wherein each of X 11 and X 12 is a fluorine atom.
9. The compound of claim 1 , wherein each of X 11 and X 12 is a chlorine atom.
10. The compound of claim 1 , wherein each of X 11 and X 12 is a fluorine atom, and each of R 12 and R 13 is a methyl group.
11. The compound of claim 1 , wherein R 12 is an ethyl group.
12. The compound of claim 1 , wherein R 13 is an ethyl group.
13. The compound of claim 1 , wherein each of R 12 and R 13 is an ethyl group.
14. The compound of claim 1 , wherein R 13 is a hydrogen atom.
15. The compound of claim 1 , wherein R 12 is a methyl group, and R 13 is a hydrogen atom.
16. The compound of claim 1 , wherein R 12 is an ethyl group, and R 13 is a hydrogen atom.
17. The compound of claim 1 , wherein R 12 is a methyl group, and R 13 is an ethyl group.
18. The compound of claim 1 , wherein R 12 is an ethyl group, and R 13 is a methyl group.
19. The compound of claim 1 , wherein (a) R 12 is a methyl group, (b) R 13 is an ethyl group, and (c) both X 11 and X 12 are fluorine atoms or both X 11 and X 12 are chlorine atoms.
20. The compound of claim 1 , wherein (a) R 12 is an ethyl group, (b) R 13 is a methyl group, and (c) both X 11 and X 12 are fluorine atoms or both X 11 and X 12 are chlorine atoms.