96551-21-2

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL 3-BROMOMETHYL-INDOLE-1-CARBOXYLATE is used as a reactant in the preparation of α,α-dialkyl-α-amino acids via enantioselective alkylation of amino acid Schiff bases. This process is crucial for the synthesis of biologically active compounds and the development of new drugs with improved therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, TERT-BUTYL 3-BROMOMETHYL-INDOLE-1-CARBOXYLATE is employed as a versatile building block for the creation of complex organic molecules. Its unique structure allows for various chemical transformations, making it a valuable component in the synthesis of specialty chemicals and advanced materials.

InChI:InChI=1/C14H16BrNO2/c1-14(2,3)18-13(17)16-9-10(8-15)11-6-4-5-7-12(11)16/h4-7,9H,8H2,1-3H3

Upstream product

• 96551-22-3 t-butyl 3-hydroxymethylindole-1-carboxylate 
• 89378-43-8 3-methyl-indole-1-carboxylic acid tert-butyl ester 
• 50624-64-1 3-(bromomethyl)-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 487-89-8 Indole-3-carboxaldehyde 
• 83-34-1 3-Methylindole 
• 34619-03-9 tert-butyldicarbonate 
• 120-72-9 indole 
• 57476-50-3 1-tert-butoxycarbonyl-3-formylindole 

Downstream Products

• 56452-52-9 α-methyl-DL-tryptophan 
• 376586-85-5 3-[3-benzyloxycarbonyloxy-1-tert-butoxycarbonyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-pyrrolidin-3-ylmethyl]-indole-1-carboxylic acid tert-butyl ester 
• 918159-90-7 (3R)-(-)-1-di(p-anisyl)methyl-3-(N-tert-butoxycarbonyl-indol-3-yl)methyl-7-chloro-1,3-dihydro-3-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one 
• 935289-88-6 tert-butyl 3-({ 6-chloro-3-oxo-4-[(1R)-1-phenylethyl]-3,4-dihydro-2-pyrazinyl}methyl)-1H-indole-1-carboxylate 
• 1072348-98-1 C₂₁H₂₃NO₄S 
• 1155864-26-8 (S)-tert-butyl 3-[2-(benzyloxy)-3-(1-methyl-1H-imidazol-2-yl)-3-oxopropyl]-1H-indole-1-carboxylate 
• 1260430-01-0 C₄₀H₃₇N₂O₅P 
• 4299-70-1 D-Tryptophan methyl ester 

Relevant academic research and scientific papers

Fusarochromene, a novel tryptophan-derived metabolite from: Fusarium sacchari

Fusarochromene isolated from the plant pathogenic fungus, Fusarium sacchari is closely related to a group of mycotoxins including fusarochromanone previously isolated from various Fusaria spp. Despite their assumed polyketide biogenesis, incorporation studies with 13C-labelled acetate, glycerol and tryptophans show that fusarochromene is unexpectedly derived via oxidative cleavage of the aromatic amino acid tryptophan. A putative biosynthetic gene cluster has been identified. This journal is

Enantioselective Enzymatic Reduction of Acrylic Acids

An ene-reductase (ERED 36) with broad substrate specificity was identified, and optimization studies led to the development of an enzymatic protocol for the reduction of α,β-unsaturated acids under mild, aqueous conditions. The substrate scope includes aromatic- A nd aliphatic-substituted acrylic acids, as well as cyclic α,β-substituted acrylic acids, yielding chiral α-substituted acids with exquisite levels of enantioselectivity (>99% ee).

Structure-Enabled Discovery of a Stapled Peptide Inhibitor to Target the Oncogenic Transcriptional Repressor TLE1

TLE1 is an oncogenic transcriptional co-repressor that exerts its repressive effects through binding of transcription factors. Inhibition of this protein–protein interaction represents a putative cancer target, but no small-molecule inhibitors have been published for this challenging interface. Herein, the structure-enabled design and synthesis of a constrained peptide inhibitor of TLE1 is reported. The design features the introduction of a four-carbon-atom linker into the peptide epitope found in many TLE1 binding partners. A concise synthetic route to a proof-of-concept peptide, cycFWRPW, has been developed. Biophysical testing by isothermal titration calorimetry and thermal shift assays showed that, although the constrained peptide bound potently, it had an approximately five-fold higher Kd than that of the unconstrained peptide. The co-crystal structure suggested that the reduced affinity was likely to be due to a small shift of one side chain, relative to the otherwise well-conserved conformation of the acyclic peptide. This work describes a constrained peptide inhibitor that may serve as the basis for improved inhibitors.

A Modular Formal Total Synthesis of (±)-Cycloclavine

Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence. (Chemical Equation Presented).

Concise synthesis of (2R,4R)-monatin

Monatin, 4-hydroxy-4-(3-indolylmethyl)-glutamic acid, is a naturally occurring sweet amino acid. The (2R,4R)-monatin isomer has been found to be the sweetest among its four stereoisomers. A concise and efficient synthesis of (2R,4R)-monatin was accomplished by the alkylation of (4R)-N-tert-butoxycarbonyl (tBoc)-4-tert-butyldimethylsilyoxy-D-pyroglutamic acid methyl ester with tert-butyl 3-(bromomethyl)-1H-indole-1-carboxylate to give (4R)-N-tBoc-4-tert-butyldimethylsilyloxy-4-(N-tBoc-3-indolylmethyl)-D-pyroglutamic acid methyl ester, i.e., the lactam form of (2R,4R)-monatin with protecting groups. This was followed by the hydrolysis of the lactam ring and deprotection. The 4-hydroxyl D-pyroglutamic acid derivative was demonstrated to be a suitable precursor for the efficient preparation of (2R,4R)-monatin in high optical purity because the alkylation proceeded in regioselective and stereoselective manners at C4 to form appropriate asymmetric tetra-substituted carbon center; the resulting alkylated pyroglutamic acid derivative was then easily converted into the linear form of monatin.

Palladium-catalyzed silylation reaction between benzylic halides and silylboronate

An efficient Pd-catalyzed silylation reaction of benzylic halides with silylboronate is reported. In this reaction, primary and secondary benzylic halides could react well with silylboronates to afford benzylic silanes. This reaction accommodates a broad substrate scope and proceeds smoothly under very mild reaction conditions. The corresponding products could be obtained in moderate to high yields and with stereospecificity.

PHENYL-UREA AND PHENYL-CARBAMATE DERIVATIVES AS INHIBITORS OF PROTEIN AGGREGATION

The present invention relates to certain phenyl-urea and phenyl-carbamate derivatives, pharmaceutical compositions containing them, and methods of using them, including methods for preventing, reversing, slowing, or inhibiting protein aggregation, and methods of treating diseases that are associated with protein aggregation, including neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, Lewy body disease, and multiple system atrophy.

Synthesis of kurasoin B using phase-transfer-catalyzed acylimidazole alkylation

The hydroxy ketone natural product kurasoin B is synthesized using a phase-transfer-catalyzed alkylation reaction with benzyloxyacetyl imidazole. A biscinchonidinium dimethylnaphthalene catalyst allowed for high yield and near complete selectivity (99% ee

Double functionalization of N-Boc-3-(tosylmethyr)indole exploiting the activating properties of the tosyl group

The anion prepared from N-Boc-3-(tosylmethyl)indole using NaH in DMF can be readily functionalized by reaction with various electrophiles. The obtained sulfonyl indoles, upon removal of the N-protecting group, undergo nucleophilic attack via a vinylogous imino derivative, leading to branched 3-substituted indoles. Georg Thieme Verlag Stuttgart.

PIPERIDINONES USEFUL IN THE TREATMENT OF INFLAMMATION

There is provided compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, m and n have meanings given in the description, and pharmaceutically acceptable derivatives thereof, which compounds are useful in the treatment of diseases and conditions associated with inflammation.