39232-85-4

Basic information

• Product Name: 5-Bromo-2-chloropyridine
• Synonyms: 1h-Indole-3ethanol,7-methyl;2-(7-Methyl-1H-indol-3-yl)ethanol;7-Methyltryptophol
• CAS NO: 39232-85-4
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• EINECS: -0
• Mol File: 39232-85-4.mol

Chemical Properties

• Melting Point: 85-86 °C
• Boiling Point: 362.2 °C at 760 mmHg
• Flash Point: 172.9 °C
• Appearance: /
• Density: 1.18 g/cm³
• Vapor Pressure: 7E-06mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 14.98±0.10(Predicted)
• CAS DataBase Reference: 5-Bromo-2-chloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-chloropyridine(39232-85-4)
• EPA Substance Registry System: 5-Bromo-2-chloropyridine(39232-85-4)

Safety Data

• Hazardous Substances Data: 39232-85-4(Hazardous Substances Data)

Usage

Uses

7-Methyltryptophol is a metabolite of Tryptophan (T947200), an essential amino acid.

InChI:InChI=1/C11H13NO/c1-8-3-2-4-10-9(5-6-13)7-12-11(8)10/h2-4,7,12-13H,5-6H2,1H3

Upstream product

• 13436-46-9 2-ethoxytetrahydrofuran 
• 635-26-7 o-tolylhydrazine hydrochloride 
• 863289-29-6 (7-Methyl-1H-indol-3-yl)-oxo-acetic acid ethyl ester 
• 1191-99-7 2,3-dihydro-2H-furan 
• 145209-21-8 trifluoromethanesulphonic acid (2-nitro-3-methylphenyl ester) 
• 59022-69-4 2-(7-methyl-1H-indol-3-yl)-2-oxoacetyl chloride 
• 933-67-5 7-methyl-1H-indole 

Downstream Products

• 41340-19-6 (1-ethyl-8-methyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 
• 863289-24-1 3-(2-bromo-ethyl)-7-methyl-1H-indole 

Relevant articles and documents

Enantioselective Construction of Spirooxindole-Fused Cyclopentanes

The present study reports an asymmetric organocatalytic cascade reaction of oxindole derivates with α,β-unsaturated aldehydes efficiently catalyzed by simple chiral secondary amine. Spirooxindole-fused cyclopentanes were produced in excellent isolated yields (up to 98%) with excellent enantiopurities (up to 99% ee) and moderate to high diastereoselectivities. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spiro compounds. In addition, a study showing the promising biological activity of selected enantioenriched products was accomplished.

Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole

We disclose herein a Au(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole. This protocol enabled the diastereoselective buildup of indole-fused azabicyclo[3.3.1]nonanes from linear precursors. Density functional theory calculations showed that the reaction proceeded via an unprecedented cascade dearomatization/rearomatization/dearomatization process. Independent gradient model analysis revealed that a noncovalent attractive interaction between the distal alkyne and the Au/proximal complex was responsible for the chemoselectivity of the first spirocyclization step.

Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds

An efficient synthesis of tetrahydrocarboline-type products and polycyclic spiroindolines has been achieved. The transformation proceeds via rhodium(II)-catalyzed intramolecular annulations of indolyl- and pyrrolyl-tethered N-sulfonyl-1,2,3-triazoles. The reaction could be tuned toward either the formal [3 + 2] cycloaddition or the C-H functionalization reaction depending on the electronic and structural features of the substrates, leading to the production of a variety of structurally related heterocyclic compounds.

Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine

Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxy, and amino groups were tolerated. From β,β-disubstituted o-nitrostyrenes, 2,3-disubstituted indoles were formed by a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterize the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine. Mild and efficient treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles through a formal reductive C(sp2)-Hamination process. A concise synthesis of a marketed drug (rizatriptan) and a formal total synthesis of aspidospermidine featuring this novel N-heterocyclization process are reported.

Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade

An enantioselective epoxidation of tryptophols followed by an intramolecular epoxide opening reaction was realized by chiral vanadium catalysts derived from C2 symmetric bis-hydroxamic acid (BHA) ligands. 3a-Hydroxyfuroindoline derivatives with up to 89% yield and 90% ee were obtained under mild reaction conditions.

3-Thio-1,2,4-triazoles, novel somatostatin sst2/sst5 agonists

Novel 3-thio-1,2,4-triazoles have been obtained via a solution-phase parallel synthesis strategy, affording potent non-peptidic human somatostatin receptor subtypes 2 and 5 agonists.

SUBSTITUTED INDOLE DERIVATIVES

Provided herein are indole derivatives, pharmaceutical compositions containing them, methods for their use, and methods for preparing these compounds.

A novel substitution reaction of tetrahydropyrano[3,4-b]indole derivative - Chain extension and structural correlation study

An unusual cyanation with rearrangement of a 1-chloromethyl-tetrahydropyrano[3,4-b]indole-1-acetic acid ester derivative is reported. The resulting C-1 chain extension product is identified by correlation studies and spectral method.