FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing a compound of formula 1, , which includes a Suzuki-Miyaura reaction, followed by Friedel-Crafts acylation, where a compound of formula 2 reacts in the presence of a palladium catalyst, a base and a compound of formula 3 (1st Suzuki-Miyaura reaction) to obtain a compound of formula 4 , the compound of formula 4 further reacts in the presence of a halogenating agent to obtain a compound of formula 5 , where X is I (5a) or Br (5b); and the compound of formula 5 further reacts in the presence of either a compound of formula (D) , or a compound of formula 7 (Sonogashira reaction), to obtain a compound of formula 8 , which further reacts in the presence of a compound of formula 9 and under Friedel-Crafts acylation conditions to obtain a compound of formula 1, where all R1, R2, R3 and R4 represent a methyl, or together with carbon atoms with which they are bonded form a phenyl ring; and R5 is -(C1-C6)alkyl.
EFFECT: novel method of producing a compound of formula 1 with high output.
4 cl, 9 ex
Title | Year | Author | Number |
---|---|---|---|
METHODS FOR OBTAINING 5-[2-[7-(TRIFLUOROMETHYL)-5-[4-(TRIFLUOROMETHYL)PHENYL]PYRAZOLO[1,5-a]PYRIMIDINE-3-YL]ETHINYL]-2-PYRIDINAMINE | 2012 |
|
RU2630700C2 |
METHOD OF IBRUTINIB PRODUCING | 2016 |
|
RU2712440C2 |
METHOD OF PRODUCING ACTIVIN-RECEPTOR-LIKE KINASE INHIBITOR | 2020 |
|
RU2826600C1 |
METHOD FOR PREPARING 1-(2-HALOGENOBIPHENYL-4-YL)-CYCLOPROPANECARBOXYLIC ACID DERIVATIVES | 2010 |
|
RU2540076C2 |
METHOD FOR PREPARATION OF THE COMPOUND 2,2-DIFLUORO-N-((1R,2S)-3-FLUORO-1-HYDROXY-1-(4-(6-(S-METHYLSULFONIMIDOYL)PYRIDINE-3-YL)PHENYL)PROPANE-2-YL)ACETAMIDE | 2019 |
|
RU2765144C1 |
PYRIMIDO[5,4-B]INDOLIZINE OR PYRIMIDO[5,4-B]PYRROLIZINE COMPOUND, METHOD FOR PRODUCTION THEREOF AND USE THEREOF | 2017 |
|
RU2721774C1 |
COUMARIN-LIKE CYCLIC COMPOUND AS MEK INHIBITOR AND USE THEREOF | 2018 |
|
RU2742234C1 |
RADIOLABELLED 2-AMINO-6-FLUORO-N-[5-FLUORO-PYRIDIN-3-YL]-PYRAZOLO [1, 5-A] PYRIMIDINE-3-CARBOXAMIDE DERIVATIVES USED AS ATR KINASE INHIBITOR, PREPARATIONS BASED THEREON COMPOUNDS AND VARIOUS SOLID FORMS THEREOF | 2015 |
|
RU2719583C2 |
METHOD OF PRODUCING 4-FORMYL-6,7-DIHYDROXY-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID ESTER | 2019 |
|
RU2722595C1 |
SYNTHESIS OF TERTBUTYL ESTER OF (4-FLUORO-3-PYPERIDIN-4-YL-BENZYL)-CARBAMIC ACID AND ITS INTERMEDIATE PRODUCTS | 2010 |
|
RU2543483C2 |
Authors
Dates
2016-02-20—Published
2011-07-18—Filed