Method for producing pyridine compound

Patent metadata

Field	Value
Publication number	US-9708341-B2
Application number	US-201515316603-A
Country	US
Kind code	B2
Filing date	May 29, 2015
Priority date	Jun 9, 2014
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

A pyridine compound represented by formula (1) that is useful as an insecticide is produced by reacting a compound represented by formula (2) and a compound represented by formula (3). In formula (2) L 1 represents a halogen atom; R 2 , R 3 , R 4 , R 5 , and R 6 represent chain hydrocarbon groups, etc., having 1-6 carbon atoms optionally substituted by fluorine atoms; A 1 represents —NR 7 —, an oxygen atom, or a sulfur atom; A 2 represents a nitrogen atom or ═CR 8 —; and R 7 and R 8 represent C1-6 chain hydrocarbon groups or hydrogen atoms. In formula (3) M + represents a sodium ion, a potassium ion, or a lithium ion.

First claim

The invention claimed is:

1. A method for preparing a pyridine compound of formula (1):

which comprises reacting a compound of formula (2):

wherein
L 1 represents a halogen atom,
R 2 , R 3 , R 4 , R 5 , and R 6 represent each independently a chain hydrocarbon group having one to six carbons which may be optionally substituted with fluorine atom(s), a phenyl group which may optionally have substituent(s), —OR 10 , —S(O) m R 10 , —S(O) 2 NR 11 R 12 , —NR 10 R 13 , —NR 11 CO 2 R 13 , —NR 11 C(O)R 12 , —CO 2 R 10 , —C(O)R 11 , —C(O)NR 11 R 12 , —SF 5 , a cyano group, a nitro group, or a hydrogen atom,
m and n are each independently an integer of 0-2,
provided that both R 5 and R 6 are not a hydrogen atom,
R 10 and R 13 represent each independently a chain hydrocarbon group having one to six carbons which may be optionally substituted with fluorine atom(s) or a phenyl group which may optionally have substituent(s),
R 11 and R 12 represent each independently a chain hydrocarbon group having one to six carbons which may be optionally substituted with fluorine atom(s), a phenyl group which may optionally have substituent(s), or a hydrogen atom,
A 1 represents —NR 7 —, an oxygen atom, or a sulfur atom,
A 2 represents a nitrogen atom or ═CR 8 —, and
R 7 and R 8 represent each independently a chain hydrocarbon group having one to six carbons, or a hydrogen atom,
wherein in the phenyl group which may optionally have substituent(s) as R 2 , R 3 , R 4 , R 5 , R 6 , R 10 , R 11 , R 12 , and R 13 , the substituent(s) is/are one or more substituent(s) selected from the group consisting of a chain hydrocarbon group having one to six carbons which may be optionally substituted with fluorine atom(s), an alkoxy group having one to six carbons which may be optionally substituted with fluorine atom(s), an alkylthio group having one to six carbons which may be optionally substituted with fluorine atom(s), an alkylsulfinyl group having one to six carbons which may be optionally substituted with fluorine atom(s), an alkylsulfonyl group having one to six carbons which may be optionally substituted with fluorine atom(s), an alkylcarbonyl group having two to six carbons which may be optionally substituted with fluorine atom(s), an alkoxycarbonyl group having two to six carbons which may be optionally substituted with fluorine atom(s), a halogen atom, a cyano group, and a nitro group,

with a compound of formula (3):

wherein
R 1 represents a chain hydrocarbon group having one to six carbons which may be optionally substituted with fluorine atom(s) or an alicyclic hydrocarbon group having three to six carbons which may be optionally substituted with fluorine atom(s), and
M + represents a sodium ion, a potassium ion, or a lithium ion,

to prepare the compound of formula (1), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A 1 , A 2 , and A 3 have the same meanings as defined above.

2. The method described in claim 1 , wherein R 2 and R 4 represent a hydrogen atom, R 3 represents a hydrogen atom or a trifluoromethyl group, R 5 represents a trifluoromethyl group, a tetrafluoroethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R 6 represents a hydrogen group, and A 2 represents a nitrogen atom or ═CH—.

3. The method described in claim 2 , wherein A 1 represents an oxygen atom, and A 2 represents ═CH—.

4. The method described in claim 2 , wherein A 1 represents —NR 7 —, R 7 represents a methyl group, and A 2 represents a nitrogen atom.

5. The method described in claim 3 , wherein R 1 represents a chain hydrocarbon group having one to six carbons.

6. The method described in claim 4 , wherein R 1 represents a chain hydrocarbon group having one to six carbons.

7. The method described in claim 1 , wherein L 1 represents a fluorine atom or a chlorine atom.

Assignees

• Sumitomo Chemical Co

Inventors

• Wakamatsu Takayuki
• Kasai Rika

Classifications

• C07D417/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D413/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title