Application of Pd-Catalyzed Cross-Coupling Reactions in the
Synthesis of
5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that
inhibit ALK5 Kinase

J 2016

Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase

TENORA, Lukáš, Juraj GALETA, Eva ŘEZNÍČKOVÁ, Vladimír KRYŠTOF, Milan POTÁČEK et. al.

Basic information

Original name

Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase

Authors

TENORA, Lukáš (203 Czech Republic, belonging to the institution), Juraj GALETA (703 Slovakia, belonging to the institution), Eva ŘEZNÍČKOVÁ (203 Czech Republic), Vladimír KRYŠTOF (203 Czech Republic) and Milan POTÁČEK (203 Czech Republic, guarantor, belonging to the institution)

Edition

The Journal of Organic Chemistry, American Chemical Society, 2016, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.849

RIV identification code

RIV/00216224:14310/16:00091403

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.joc.6b02230

UT WoS

000389396400032

Keywords in English

Cross-Coupling reactions; Pd catalysed; 4H-pyrrolo[1;2-b]pyrazoles; ALK5 Kinase inhibitors;

Abstract

V originále

C-H activation of position 3 of a substituted pyrazole ring catalyzed by palladium(II) was straightforward and convenient for arylated or heteroarylated 5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles. Moreover, we introduced simple protection of the nitrogen in the pyridin-2-yl directing group, which otherwise does not allow cross-coupling reaction, by transformation to the N-oxide. Selected final products were reasonably selective ALK5 kinase inhibitors.

Citovat

TENORA, Lukáš, Juraj GALETA, Eva ŘEZNÍČKOVÁ, Vladimír KRYŠTOF and Milan POTÁČEK. Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase. The Journal of Organic Chemistry. American Chemical Society, 2016, vol. 81, No 23, p. 11841-11856. ISSN 0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.6b02230.

@article{1358648,
   author = {Tenora, Lukáš and Galeta, Juraj and Řezníčková, Eva and Kryštof, Vladimír and Potáček, Milan},
   article_number = {23},
   doi = {http://dx.doi.org/10.1021/acs.joc.6b02230},
   keywords = {Cross-Coupling reactions; Pd catalysed; 4H-pyrrolo[1;2-b]pyrazoles; ALK5 Kinase inhibitors;},
   language = {eng},
   issn = {0022-3263},
   journal = {The Journal of Organic Chemistry},
   title = {Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase},
   url = {http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02230},
   volume = {81},
   year = {2016}
}

TY  - JOUR
ID  - 1358648
AU  - Tenora, Lukáš - Galeta, Juraj - Řezníčková, Eva - Kryštof, Vladimír - Potáček, Milan
PY  - 2016
TI  - Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase
JF  - The Journal of Organic Chemistry
VL  - 81
IS  - 23
SP  - 11841-11856
EP  - 11841-11856
PB  - American Chemical Society
SN  - 00223263
KW  - Cross-Coupling reactions
KW  - Pd catalysed
KW  - 4H-pyrrolo[1;2-b]pyrazoles
KW  - ALK5 Kinase inhibitors;
UR  - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02230
L2  - http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02230
N2  - C-H activation of position 3 of a substituted pyrazole ring catalyzed by palladium(II) was straightforward and convenient for arylated or heteroarylated 5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles. Moreover, we introduced simple protection of the nitrogen in the pyridin-2-yl directing group, which otherwise does not allow cross-coupling reaction, by transformation to the N-oxide. Selected final products were reasonably selective ALK5 kinase inhibitors.
ER  -

TENORA, Lukáš, Juraj GALETA, Eva ŘEZNÍČKOVÁ, Vladimír KRYŠTOF and Milan POTÁČEK. Application of Pd-Catalyzed Cross-Coupling Reactions in the Synthesis of 5,5-Dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles that inhibit ALK5 Kinase. \textit{The Journal of Organic Chemistry}. American Chemical Society, 2016, vol.~81, No~23, p.~11841-11856. ISSN~0022-3263. Available from: https://dx.doi.org/10.1021/acs.joc.6b02230.

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