Method for producing amide derivative

1. A method of producing an amide derivative represented by the following Formula (3):

wherein, in Formula (3), X 1 , X 3 , X 4 , X 5 , A, T, Y 1 , Y 2 , R 1 , R 2 , and Rf have the same definitions as X 1 , X 3 , X 4 , X 5 , A, T, Y 1 , Y 2 , R 1 , R 2 , and Rf in Formula (1) and Formula (2) shown below, respectively,

the method comprising allowing a compound represented by the following Formula (1) and a compound represented by the following Formula (2) to react with each other:

wherein, in Formula (1), Y 1 represents a bromine atom or an iodine atom; Y 2 represents trifluoromethyl group; Rf represents a perfluoropropyl group; and R 1 represents a hydrogen atom or a methyl group; and

wherein, in Formula (2), LG represents a leaving group; T represents a hydrogen atom or a fluorine atom; R 2 represents a hydrogen atom or a methyl group; X 1 represents a hydrogen atom or a chlorine atom; X 3 and X 4 each independently represent a hydrogen atom, a fluorine atom or a cyano group; X 5 represents a hydrogen atom and A represents a nitrogen atom or a methine group.

2. The method of producing an amide derivative according to claim 1 , wherein, in Formula (2), the leaving group represented by LG is a halogen atom.

3. The method of producing an amide derivative according to claim 2 , wherein the amide derivative represented by Formula (3) is a compound represented by the following Formula (4):

wherein, in Formula (4), X 1 represents a hydrogen atom or a chlorine atom; X 2 and X 5 each represent a hydrogen atom; X 3 and X 4 and each independently represent a hydrogen atom, a fluorine atom, or a cyano group; R 1 and R 2 each independently represent a hydrogen atom or a methyl group; Y 1 represents a bromine atom or an iodine atom; Y 2 represents a trifluoromethyl group; and Rf represents a perfluoropropyl group.

4. The method of producing an amide derivative according to claim 3 , further comprising allowing a compound represented by the following Formula (5) and a compound represented by the following Formula (6) or (7) to react with each other, thereby producing a compound represented by the following Formula (8):

wherein, in Formula (5), R 2 represents a hydrogen atom or a methyl group; and R 3 represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 3 -C 8 cycloalkyl group, a C 2 -C 6 alkenyl group, or a C 2 -C 6 alkynyl group;

wherein, in Formula (6), X 1 represents a hydrogen atom or a chlorine atom; X 2 and X 5 each represent a hydrogen atom; X 3 and X 4 each independently represent a hydrogen atom, a fluorine atom, or a cyano group; and LG represents a leaving group;

wherein, in Formula (7), X 1 represents a hydrogen atom or a chlorine atom; X 2 and X 5 each represent a hydrogen atom; X 3 and X 4 each independently represent a hydrogen atom, a fluorine atom, or a cyano group; and

wherein, in Formula (8), R 2 and R 3 have the same definitions as R 2 and R 3 in Formula (5), respectively; and X 1 , X 2 , X 3 , X 4 , and X 5 have the same definitions as X 1 , X 2 , X 3 , X 4 , and X 5 in Formula (6) or Formula (7), respectively.

5. The method of producing an amide derivative according to claim 4 , further comprising alkylating a compound represented by Formula (8) and in which R 2 represents a hydrogen atom, thereby producing a compound represented by the following Formula (9):

wherein, in Formula (9), R 21 represents a C 1 -C 6 alkyl group; and R 3 , X 1 , X 2 , X 3 , X 4 , and X 5 have the same definitions as R 3 , X 1 , X 2 , X 3 , X 4 , and X 5 in Formula (8), respectively.

6. The method of producing an amide derivative according to claim 4 , further comprising converting a compound represented by Formula (5) and in which R 2 represents a hydrogen atom, to a compound represented by the following Formula (10):

wherein, in Formula (10), R 21 represents a C 1 -C 6 alkyl group; and R 3 has the same definition as R 3 in Formula (8).

7. The method of producing an amide derivative according to claim 4 , further comprising converting a compound represented by Formula (8) and in which R 3 represents a C 1 -C 6 alkyl group, a C 3 -C 8 cycloalkyl group, a C 2 -C 6 alkenyl group, or a C 2 -C 6 alkynyl group, to a compound represented by the following Formula (11):

wherein, in Formula (11), X 1 , X 2 , X 3 , X 4 , X 5 , and R 2 have the same definitions as X 1 , X 2 , X 3 , X 4 , X 5 , and R 2 in Formula (8), respectively.

8. The method of producing an amide derivative according to claim 7 , further comprising converting the compound represented by Formula (11) to a compound represented by the following Formula (12):

wherein, in Formula (12), X 1 , X 2 , X 3 , X 4 , X 5 , and R 2 have the same definitions as X 1 , X 2 , X 3 , X 4 , X 5 , and R 2 in Formula (11), respectively; and Hal represents a fluorine atom, a chlorine atom, or a bromine atom.

9. The method of producing an amide derivative according to claim 2 , wherein the amide derivative represented by Formula (3) is a compound represented by the following Formula (20):

wherein, in Formula (20), X 1 represents a hydrogen atom or a chlorine atom, X 3 and X 4 each independently represent a hydrogen atom, a fluorine atom, or a cyano group, and X 5 represents a hydrogen atom, provided that at least one of X 1 or X 3 represents a halogen atom; R 1 represents a hydrogen atom or a methyl group; R 2 represents a hydrogen atom or a methyl group; Y 1 represents a bromine atom or an iodine atom; Y 2 represents a trifluoromethyl group and Rf represents a perfluoropropyl group.