Method for manufacturing 3-(alkylsulfonyl)pyridine-2-carboxylic acid

Patent metadata

Field	Value
Publication number	US-9815786-B2
Application number	US-201515318551-A
Country	US
Kind code	B2
Filing date	Jun 22, 2015
Priority date	Jun 26, 2014
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

A compound represented by formula (7):

or a salt thereof can be manufactured by the following steps:
a step of allowing a compound represented by formula (1-S):

to react with a compound represented by formula (2):

R 2 SM 2   (2)

to give a compound represented by formula (3-S):

a step of allowing the compound represented by formula (3-S) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-S) or a salt thereof:

and
a step of reducing the compound represented by formula (6-S) or salt thereof in the presence of a base and a heterogeneous transition metal catalyst to give a compound represented by formula (7) or a salt thereof, wherein X, R 1 , R 2 , and M 2 are defined in the specification.

First claim

The invention claimed is:

1. A method for producing a compound represented by formula (7) or a salt thereof, comprising:
a step of allowing a compound represented by formula (1-S):

wherein R 1 represents a C 1-8 straight-chain alkyl group, and X represents a halogen atom,
to react with a compound represented by formula (2):
R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-S):

wherein R 1 , R 2 , and X are as defined above;
a step of allowing the compound represented by formula (3-S) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-S) or a salt thereof:

wherein X and R 2 are as defined above; and
a step of reducing the compound represented by formula (6-S) or salt thereof in the presence of a base and a heterogeneous transition metal catalyst to give a compound represented by formula (7) or a salt thereof:

wherein R 2 is as defined above.

2. A method for producing a compound represented by formula (7) or a salt thereof, comprising:
a step of allowing a compound represented by formula (4):

wherein X represents a halogen atom, and Y represents a halogen atom, to react with a compound represented by formula (5):
R 1 SM 1   (5)

wherein R 1 represents a C 1-8 straight-chain alkyl group, and M 1 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (1-S):

wherein R 1 and X are as defined above;
a step of allowing the compound represented by formula (1-S) to react with a compound represented by formula (2):
R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-S):

wherein R 1 , R 2 , and X are as defined above;
a step of allowing the compound represented by formula (3-S) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-S):

wherein X and R 2 are as defined above; and
a step of reducing the compound represented by formula (6-S) or a salt thereof in the presence of a base and a heterogeneous transition metal catalyst to give a compound represented by formula (7) or a salt thereof:

wherein R 2 is as defined above.

3. A method for producing a compound represented by formula (6-S) or a salt thereof, comprising:
a step of allowing a compound represented by formula (1-S):

wherein R 1 represents a C 1-8 straight-chain alkyl group, and X represents a halogen atom,
to react with a compound represented by formula (2):
R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-S):

wherein R 1 , R 2 , and X are as defined above; and
a step of allowing the compound represented by formula (3-S) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-S) or a salt thereof:

wherein X and R 2 are as defined above.

4. A method for producing a compound represented by formula (6-S) or a salt thereof, comprising:
a step of allowing a compound represented by formula (4):

wherein X represents a halogen atom, and Y represents a halogen atom, to react with a compound represented by formula (5):
R 1 SM 1   (5)

wherein R 1 represents a C 1-8 straight-chain alkyl group, and M 1 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (1-S):

wherein R 1 and X are as defined above;
a step of allowing the compound represented by formula (1-S) to react with a compound represented by formula (2):
R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-S):

wherein R 1 , R 2 , and X are as defined above; and
a step of allowing the compound represented by formula (3-S) to react with hydrogen peroxide in the presence of a tungsten catalyst and an acid to give a compound represented by formula (6-S):

wherein X and R 2 are as defined above.

5. A method for producing a compound represented by formula (3-S), comprising allowing a compound represented by formula (1-S):

wherein R 1 represents a C 1-8 straight-chain alkyl group, and X represents a halogen atom,
to react with a compound represented by formula (2):
R 2 SM 2   (2)

wherein R 2 represents a C 1-8 straight-chain alkyl group, and M 2 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (3-S):

wherein R 1 , R 2 , and X are as defined above.

6. A method for producing a compound represented by formula (3-S), comprising:
a step of allowing a compound represented by formula (4):

wherein X represents a halogen atom, and Y represents a halogen atom,
to react with a compound represented by formula (5):
R 1 SM 1   (5)

wherein R 1 represents a C 1-8 straight-chain alkyl group, and M 1 represents a hydrogen atom or an alkali metal,
to give a compound represented by formula (1-S):

wherein R 1 and X are as defined above; and
a step of a

Assignees

• Sumitomo Chemical Co

Inventors

• Kimura Takahiro
• Maehata Ryota

Classifications

• C07D213/81

  Amides; Imides · CPC title

• C07D213/78

  Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D213/807 Primary

  by oxidation of pyridines or condensed pyridines · CPC title

• A61K31/44

  Non condensed pyridines; Hydrogenated derivatives thereof · CPC title

• C07D213/803 Primary

  Processes of preparation · CPC title