IP Library Granted Patent US 9,359,304
Granted Patent B2
US 9,359,304 · App. 13/816,161 · Granted Jun 7, 2016

Process for the preparation of 3-haloalkylpyrazoles

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Quick Facts
Patent No.
US 9,359,304
App. No.
13/816,161
Granted
Jun 7, 2016
Kind
B2
Abstract

The present invention provides a process for the preparation of a compound of formula (I) wherein R 1 is C 1 -C 4 haloalkyl; R 2 is optionally substituted alkyl, optionally substituted aryl or optionally substituted heteroaryl; and R 3 is methyl or ethyl; comprising reacting a compound of formula (IV) wherein R 1 , R 2 and R 3 are as defined for the compound of formula I; with an alkylating agent in the presence of an amide.

Claims (31)

1. A process for the preparation of a compound of formula I:

wherein R 1 is C 1 -C 4 haloalkyl;

R 2 is optionally substituted alkyl, optionally substituted aryl or optionally substituted heteroaryl; and

R 3 is methyl or ethyl;

comprising reacting a compound of formula II:

wherein R 1 and R 2 are as defined for the compound of formula I;

with an alkylating agent in the presence of an amide;

wherein the process comprises N alkylating the compound of formula II and isomerising the compound of formula IV

wherein R 1 , R 2 and R 3 are as defined for the compound of formula I;

produced from the alkylation at substantially same time;

wherein the alkylating agent is a compound of formula III:

wherein R 3 is methyl or ethyl;

wherein the amide is present in an amount of 0.1 molar equivalents to 10 molar equivalents relative to the amount of the compound of formula IV and the compound of formula I.

2. A process according to claim 1 , wherein the amide is a tertiary amide.

3. A process according to claim 1 , wherein the amide is a compound of formula XX:

wherein R 4 is H or C 1 -C 4 alkyl;

R 5 is C 1 -C 4 alkyl;

R 6 is C 1 -C 4 alkyl;

or R 4 and R 5 together are C 2 -C 5 alkyene;

or R 5 and R 6 are together C 2 -C 5 alkyene.

4. A process according to claim 1 , wherein the amide is dimethylformamide, N-methyl-2-pyrollidone or N, N-dimethylacetamide.

5. A process according to claim 1 , wherein the alkylating agent is capable of alkylating a compound of formula IV as defined in claim 1 to form a compound of formula IVa

wherein R 1 , R 2 and R 3 are as defined for a compound of formula IV in claim 1 .

6. A process according to claim 1 , wherein the process is for preparing a compound of formula VI:

comprising reacting a compound of formula VII:

with a compound of formula VIII:

in the presence of an amide selected from dimethylformamide, N-methyl-2-pyrollidone and N,N-dimethylacetamide.

7. A process according to claim 1 , wherein

R 1 is difluoromethyl or trifluoromethyl;

R 2 is C 1 -C 6 alkyl; and

R 3 is methyl.

Assignments (2)
MERGER AND CHANGE OF NAME Recorded Mar 14, 2025
From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 070516/0868 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2013
From: WANG, LINHUA; SHETH, RITESH BHARAT
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 031765/0522 →