FIELD: chemistry.
SUBSTANCE: invention relates to an improved method of producing a compound of formula , comprising the steps: 1) reacting a compound of formula , where X is a fluorine atom, and X1 is selected from a group consisting of chlorine, bromine and iodine atoms and a triflate group (CF3SO3), with a compound of formula , where R denotes two chlorine atoms, in the presence of a palladium catalyst to form a compound of formula ; 2) radical bromination of the compound of formula (IV) with N-bromosuccinimide in the presence of a catalytic amount of benzoyl peroxide to form a compound of formula ; 3) converting the compound of formula (V) to the corresponding nitrile derivative of formula ; 4) reacting the compound of formula (VI) with 1,2-dibromoethane to form a compound of formula ; and 5) hydrolysis of the compound of formula (VII) to obtain a compound of formula (Ia).
EFFECT: invention provides higher output of the compound with higher chemical purity without a chromatographic purification step.
8 cl, 5 ex
Title | Year | Author | Number |
---|---|---|---|
METHOD FOR PREPARING 1-(2-HALOGENOBIPHENYL-4-YL)-CYCLOPROPANECARBOXYLIC ACID DERIVATIVES | 2010 |
|
RU2540076C2 |
METHOD OF PRODUCING PHENYL-SUBSTITUTED HETEROCYCLIC DERIVATIVE THROUGH COUPLING USING TRANSITION METAL AS CATALYST | 2010 |
|
RU2510393C9 |
CONDENSED CYCLIC COMPOUNDS | 2007 |
|
RU2444521C2 |
PREPARATION OF SUBSTITUTED INDENES | 2003 |
|
RU2323921C2 |
COUPLING REACTIONS POSSIBLY USED IN SYNTHESIS OF (1H-TETRAZOL-5-YL)BIPHENYL DERIVATIVES | 2005 |
|
RU2426728C2 |
HALOGEN-SUBSTITUTED HETEROCYCLIC COMPOUND | 2013 |
|
RU2756506C2 |
HALOGEN SUBSTITUTED HETEROCYCLIC COMPOUND | 2013 |
|
RU2649398C2 |
HALOGEN SUBSTITUTED HETEROCYCLIC COMPOUND SALT | 2015 |
|
RU2689315C2 |
SUBSTITUTED CARBOCYCLIC AMIDES, METHODS OF PREPARATION THEREOF, INDANE DERIVATIVES, PHARMACEUTICAL COMPOSITION AND METHODS OF PROPHYLAXIS OR MEDICAL TREATMENT | 1995 |
|
RU2145954C1 |
4-OXO-1-(3-SUBSTITUTED PHENYL)-1,4-DIHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXAMIDES, PHARMACEUTICAL COMPOSITIONS BASED ON THEREOF, METHOD FOR TREATMENT AND PROPHYLAXIS AND METHOD FOR IMPROVING COGNITIVE ABILITY IN HEALTH SUBJECT | 2003 |
|
RU2312865C2 |
Authors
Dates
2013-12-27—Published
2009-05-08—Filed