1-[2-(1H-Indol-3-YL)ethyl]-3-(methoxycarbonyl)pyridin-1-ium bromide

Base Information

• Chemical Name: 1-[2-(1H-Indol-3-YL)ethyl]-3-(methoxycarbonyl)pyridin-1-ium bromide
• CAS No.: 4695-86-7
• Molecular Formula: C17H17N2O2+
• Molecular Weight: 281.3285
• ChEMBL ID: CHEMBL1381300
• DSSTox Substance ID: DTXSID60963703
• NSC Number: 165249
• Mol file: 4695-86-7.mol

Synonyms:4695-86-7;MLS000728592;CHEMBL1381300;SCHEMBL10871771;DTXSID60963703;HMS2270M22;NSC165249;1-[2-(1H-INDOL-3-YL)ETHYL]-3-(METHOXYCARBONYL)PYRIDIN-1-IUM BROMIDE;NSC-165249;SMR000470779

Chemical Property of 1-[2-(1H-Indol-3-YL)ethyl]-3-(methoxycarbonyl)pyridin-1-ium bromide

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 360.04734
• Heavy Atom Count: 22
• Complexity: 361

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C[N+](=CC=C1)CCC2=CNC3=CC=CC=C32.[Br-]

Technology Process of 1-[2-(1H-Indol-3-YL)ethyl]-3-(methoxycarbonyl)pyridin-1-ium bromide

There total 5 articles about 1-[2-(1H-Indol-3-YL)ethyl]-3-(methoxycarbonyl)pyridin-1-ium bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

methyl 3-pyridinecarboxylate (93-60-7) + 3-(2-bromoethyl)-1H-indole (3389-21-7) → 3-methoxycarbonyl-1-[2-(3-indolyl)ethyl]pyridinium bromide (4695-86-7)

Guidance literature:

In neat (no solvent); at 70 ℃; for 8h; Inert atmosphere;

DOI:10.3987/COM-17-13822

Reference yield:

indole (120-72-9) → 3-methoxycarbonyl-1-[2-(3-indolyl)ethyl]pyridinium bromide (4695-86-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diethyl ether / 6 h / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

3.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.1: neat (no solvent) / 8 h / 70 °C / Inert atmosphere

With lithium aluminium tetrahydride; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: |Friedel-Crafts Acylation;

DOI:10.3987/COM-17-13822

Reference yield:

2-(3-indolyl)oxoacetic acid methyl ester (18372-22-0) → 3-methoxycarbonyl-1-[2-(3-indolyl)ethyl]pyridinium bromide (4695-86-7)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2: triphenylphosphine; carbon tetrabromide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3: neat (no solvent) / 8 h / 70 °C / Inert atmosphere

With lithium aluminium tetrahydride; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.3987/COM-17-13822

upstream raw materials:

methyl 3-pyridinecarboxylate

3-(2-bromoethyl)-1H-indole

indole

2-(3-indolyl)oxoacetic acid methyl ester

Downstream raw materials:

Vallesiachotamin

Isovallesiachotamin

(+/-)-vallesiachotaminen

dihydrovallesiachotamine

Refernces

• 1、 Wang, Shou-Guo,Xia, Zi-Lei,Xu, Ren-Qi,Liu, Xi-Jia,Zheng, Chao,You, Shu-Li. "Construction of Chiral Tetrahydro-β-Carbolines: Asymmetric Pictet–Spengler Reaction of Indolyl Dihydropyridines". supporting information. p. 7440 - 7443. Retrieved 2017/06/13.