64622-16-8

Basic information

• Product Name: AKOS MSC-0782
• Synonyms: AKOS MSC-0782;2-BROMO-6-CHLOROBENZALDEHYDE;Benzaldehyde, 2-broMo-6-chloro-;2-Bromo-6-chlorobenzaldehyde≥ 98% (GC)
• CAS NO: 64622-16-8
• Molecular Formula: C₇H₄BrClO
• Molecular Weight: 219.47
• Mol File: 64622-16-8.mol

Chemical Properties

• Melting Point: 74-76℃
• Boiling Point: 258.819°C at 760 mmHg
• Flash Point: 110.33°C
• Appearance: /Solid
• Density: 1.698g/cm³
• Vapor Pressure: 0.013mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: AKOS MSC-0782(CAS DataBase Reference)
• NIST Chemistry Reference: AKOS MSC-0782(64622-16-8)
• EPA Substance Registry System: AKOS MSC-0782(64622-16-8)

Safety Data

• Hazardous Substances Data: 64622-16-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
AKOS MSC-0782 is used as a linker in the Buchwald C-N bond forming reaction for the preparation of Bruton's tyrosine kinase inhibitor, a drug that targets the treatment of B-cell malignancies and autoimmune diseases. Its role as a linker provides higher selectivity and reactivity in the reaction, ensuring the successful synthesis of the desired compound.

InChI:InChI=1/C7H4BrClO/c8-6-2-1-3-7(9)5(6)4-10/h1-4H

Upstream product

• 62356-27-8 2-bromo-6-chlorotoluene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 89-98-5 2-chloro-benzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 1673-76-3 3-(2-bromo-6-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 928048-11-7 3-chloro-2-carbaldehyde phenylboronic acid 
• 793706-90-8 2-chloro-6-(4-pyridyl)benzaldehyde 
• 1243602-09-6 ethyl (Z)-2-bromo-3-(2-bromo-6-chlorophenyl)acrylate 
• 1243601-90-2 1-bromo-2-[(E)-2-bromovinyl]-3-chlorobenzene 
• 1263357-63-6 C₁₆H₁₈BrClN₂O₃ 
• 1263357-62-5 C₁₅H₁₆BrClN₂O₃ 
• 1296216-50-6 benzyl 2-(2-bromo-6-chlorophenyl)-1,2,3,6-tetrahydropyridine-1(2H)-carboxylate 
• 1296216-53-9 10-(4-(trifluoromethyl)phenyl)-1,10b-dihydropyrido[2,1-a]isoindol-6(4H)-one 
• 1296216-54-0 10-(4-methoxy-phenyl)-1,10b-dihydro-4H-pyrido[2,1-a]isoindol-6-one 
• 1296216-56-2 10-(4-trifluoromethyl-phenyl)-1,3,4,10b-tetrahydro-2H-pyrido[2,1-a]isoindol-6-one 
• 1296216-47-1 allyl-[1-(2-bromo-6-chloro-phenyl)-but-3-enyl]-carbamic acid benzyl ester 
• 1296216-84-6 2-(2-bromo-6-chloro-phenyl)-3,4-dihydro-2H-pyridine-1-carboxylic acid benzylester 
• 1296216-87-9 7-bromo-2-(2-bromo-6-chloro-phenyl)-3,4,4a,5,6,10b-hexahydro-2Hbenzo[h][1,6]naphthyridine-1,5-dicarboxylic acid 1-benzyl ester 5-ethyl ester 

Relevant articles and documents

Discovery of N-(Indazol-3-yl)piperidine-4-carboxylic Acids as ROR?3t Allosteric Inhibitors for Autoimmune Diseases

The clinical success of anti-IL-17 monoclonal antibodies (i.e., Cosentyx and Taltz) has validated Th17 pathway modulation for the treatment of autoimmune diseases. The nuclear hormone receptor RORγt is a master regulator of Th17 cells and affects the prod

Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes

We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.

Palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes via a monodentate transient directing group strategy

A facile and efficient monodentate transient directing group strategy was developed to enable the palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes. A broad scope of benzaldehydes were transformed into the desired products by employing 2-amino-5-chlorobenzotrifluoride as a monodentate transient directing group, demonstrating good functional group tolerance. Mild reaction conditions and no requirement for a silver salt are also features of this strategy.

Synthesis of N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C–N Cross-coupling

A number of β-enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β-diketones. Two general protocols for their palladium-catalyzed intramolecular C–N cross-coupling were established to give corresponding N-substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.

Diverse ortho-C(sp2)-H functionalization of benzaldehydes using transient directing groups

Pd-catalyzed C-H functionalizations promoted by transient directing groups remain largely limited to C-H arylation only. Herein, we report a diverse set of ortho-C(sp2)-H functionalizations of benzaldehyde substrates using the transient directing group strategy. Without installing any auxiliary directing group, Pd(II)-catalyzed C-H arylation, chlorination, bromination, and Ir(III)-catalyzed amidation, could be achieved on benzaldehyde substrates. The transient directing groups formed in situ via imine linkage can override other coordinating functional groups capable of directing C-H activation or catalyst poisoning, significantly expanding the scope for metal-catalyzed C-H functionalization of benzaldehydes. The utility of this approach is demonstrated through multiple applications, including late-stage diversification of a drug analogue.

N-ALKYLATED INDOLE AND INDAZOLE COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF

The present invention relates to compounds according to Formula I and pharmaceutically acceptable salts or solvates thereof. Such compounds can be used in the treatment of RORgammaT-mediated diseases or conditions.

Development of a scalable synthesis of a Bruton's tyrosine kinase inhibitor via C-N and C-C bond couplings as an end game strategy

A scalable and convergent synthesis of a BTK (Bruton's tyrosine kinase) inhibitor has been developed. Synthetic routes to key intermediates were explored for the scale-up campaign, especially the process for 6-dimethylaminodihydroisoquinolinone, which was prepared via a regioselective cyclization of an isocyanate, mediated by AlCl3. Improved routes to key building blocks were demonstrated by expedient multikilogram productions. The target compound was assembled through a Pd-catalyzed amidation reaction followed by a Suzuki-Miyaura cross-coupling reaction.

N-ALKYLATED INDOLE AND INDAZOLE COMPOUNDS AS RORgammaT INHIBITORS AND USES THEREOF

The present invention relates to compounds according to Formula I and pharmaceutically acceptable salts or solvates thereof. Such compounds can be used in the treatment of RORgammaT-mediated diseases or conditions.

Selective ortho -bromination of substituted benzaldoximes using Pd-catalyzed C-H activation: Application to the synthesis of substituted 2-bromobenzaldehydes

Substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a three-step sequence involving a selective palladium-catalyzed ortho-bromination as the key step. O-Methyloxime serves as a directing group in this reaction. A rapid deprotection of substituted 2-bromobenzaldoximes afforded substituted 2-bromobenzaldehydes with good overall yields.

METHODS FOR STABILIZING LITHIATED HALOGEN-SUBSTITUTED AROMATIC COMPOUNDS

The present invention provides novel methods for stabilizing lithiated halogen-substituted aromatic compounds. In particular, the method is useful for the preparation of 2-methoxy-5, 6-difluorobenzaldehyde, an important intermediate for the preparation of