219580-32-2

Usage

Uses

Used in Pharmaceutical Industry:
Tert-Butyl 1H-pyrazole-1-carboxylate is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex molecular structures. Its presence in the synthesis process aids in the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic chemistry, tert-Butyl 1H-pyrazole-1-carboxylate is used as a building block for the creation of other organic compounds. Its reactivity and structural features make it a valuable component in the synthesis of a range of chemical products, including those with potential applications in materials science and specialty chemicals.

InChI:InChI=1/C8H12N2O2/c1-8(2,3)12-7(11)10-6-4-5-9-10/h4-6H,1-3H3

Upstream product

• 102-52-3 malonaldehydebis(dimethylacetal) 
• 870-46-2 t-butoxycarbonylhydrazine 
• 288-13-1 NH-pyrazole 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 14719-37-0 ethyl 2-(tert-butoxycarbonylamino)acetate 
• 552846-17-0 tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate 
• 288-13-1 NH-pyrazole 
• 169512-94-1 (+/-)-N-tert-butoxycarbonyl-α-phenylglycine methyl ester 

Relevant academic research and scientific papers

Access to Silylated Pyrazole Derivatives by Palladium-Catalyzed C?H Activation of a TMS group

A simple and efficient approach to new silylated heterocycles of potential interest in medicinal chemistry is presented. A set of bromophenyl trimethylsilyl pyrazole intermediates can be transformed by direct organometallic routes into two families of regioisomeric iodoaryl substrates; using either arylzinc or aryllithium chemistry, the TMS group remains on the pyrazole ring or translocates to the aryl moiety. These two families can then be efficiently transformed into benzo silino pyrazoles thanks to a single-step cyclization relying on the Pd-catalyzed activation of a non-activated C(sp3)?H bond alpha to a silicon atom. The experimental conditions used, which are fully compatible with the pyrazole ring, suggest that this reaction evolves through a concerted metalation–deprotonation (CMD) mechanism.

Synthesis of substituted-3-iodo-1H-pyrazole derivatives and their further modification under Sonogashira cross-coupling reaction conditions

A convenient synthetic route for preparation of valuable synthetic intermediates - 1-(1-ethoxyethyl)-3-iodo-1H-pyrazole derivatives has been developed. During this work protection reaction of N-H bond in substituted 3-iodo-1H-pyrazole derivatives with ethyl vinyl ether and migration of ethoxyethyl protecting group was investigated. Synthetic possibilities of Sonogashira cross-coupling reactions of substituted 1-(1-ethoxyethyl)-3-iodo-1H-pyrazole derivatives with phenylacetylene were studied and evaluated.

A highly chemoselective Boc protection of amines using sulfonic-acid-functionalized silica as an efficient heterogeneous recyclable catalyst

A facile and versatile method for the chemoselective Boc protection of amines has been developed by a treatment with (Boc)2O in the presence of sulfonic-acid-functionalized silica as a catalyst. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines; aminols, amino-esters; and sulfonamides. The catalyst works under heterogeneous conditions and can be recycled.

New facile alkoxycarbonylating agent, alkyl pyrazole-1-carboxylates. The preparation and the utilities

Alkyl pyrazole-1-carboxylates (2), which were readily prepared from alkyl chloroformate or carbazate in good yields, were provided as the new facile alkoxycarbonylating agents toward the Grignard reagents for the synthesis of one carbon higher carboxylic esters. Also amines were alkoxycarbonylated by 2 to produce the corresponding urethanes even in an aqueous medium. Benzyl 3,5-dimethylpyrazole-1-carboxylate (2d) could be utilized for the Cbz-protection of amino acids and esters in good yield without any racemization.