459133-69-8

Usage

Uses

Used in Pharmaceutical Research and Development:
3-IODO-5-NITRO-1H-INDAZOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is used as a precursor in the synthesis of new pharmaceuticals due to its potential to contribute to the development of compounds with significant biological activity.
Used in Organic Chemistry Research:
In the field of organic chemistry, 3-IODO-5-NITRO-1H-INDAZOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER is employed as a research tool, facilitating the exploration of new synthetic pathways and the creation of novel organic compounds. Its tert-butyl ester functionality provides a stable and easily manipulated platform for conducting various chemical reactions and studies.

InChI:InChI=1/C12H12IN3O4/c1-12(2,3)20-11(17)15-9-5-4-7(16(18)19)6-8(9)10(13)14-15/h4-6H,1-3H3

Upstream product

• 5401-94-5 5-nitroindazole 
• 34619-03-9 tert-butyldicarbonate 
• 70315-69-4 3-iodo-5-nitro-1H-indazole 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1294513-85-1 C₂₃H₂₄N₄O 
• 1294513-87-3 C₂₃H₁₈N₄O 

Relevant academic research and scientific papers

Suzuki-type cross-coupling reaction of unprotected 3-iodoindazoles with pinacol vinyl boronate: An expeditive C-3 vinylation of indazoles under microwave irradiation

Herein we report an expeditive C-3 vinylation of unprotected 3-iodoindazoles under microwave irradiation. Ten C-5 substituted 3-vinylindazole derivatives, nine of them novel, were synthesized through this method, which proceeds in moderate to excellent yields starting from C-5 substituted 3-iodoindazole derivatives. In all cases, the C-3 vinylated derivative was the only isolated product. This methodology allows access to 3-vinylated indazoles selectively and directly without the need of N-protection. 3-Vinylindazoles could be interesting synthetic intermediates allowing access to biologically active molecules.

Optimisation of ITK inhibitors through successive iterative design cycles

Based on a hit cluster of compounds inhibiting interleukin-2 inducible T-cell kinase (ITK) in the submicromolar range a series of ITK inhibitor libraries were synthesized. Through iterative design cycles including kinase crystal structure information, indolylindazole libraries were identified which showed low nanomolar activity in enzymatic and cellular assays. The potential of these novel lead series was confirmed through in vivo tests in an anti-CD3-IL2 mouse model. The intravenous administration of highly potent ITK inhibitor 11o resulted in dose-dependent, efficient suppression of IL-2.

NOVEL SUBSTITUTED INDAZOLES, THE PREPARATION THEREOF AND USE OF SAME IN THERAPEUTICS

This disclosure relates to compounds of formula (I): wherein R1, R2, R3, R4, E, and n1 are as defined in the disclosure, to compositions containing them, to processes for preparing them, and the use t

6-AMINO-PYRIMIDINE-4-CARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS WHICH BIND TO THE SPHINGOSINE 1-PHOSPHATE (S1P) RECEPTOR FOR THE TREATMENT OF MULTIPLE SCLEROSIS

The invention relates to compounds of formula (I): wherein X, W, Q, R, R1 and R2 have the meanings given in claim 1. The compounds are useful e.g. in the treatment of autoimmune disorders, such as multiple sclerosis.

Sonogashira cross-coupling reaction of 3-iodoindazoles with various terminal alkynes: A mild and flexible strategy to design 2-aza tryptamines

This paper describes a Sonogashira-type cross-coupling reaction of 3-iodoindazoles with various terminal alkynes as a general route to 3-alkynylindazoles. The coupling reaction is illustrated by the preparation of new indazolylpropiolic or propargylic derivatives. Scope and limitation of the method are outlined.