[2-(5-Bromo-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [2-(5-Bromo-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 174021-63-7
• Molecular Formula: C15H19BrN2O2
• Molecular Weight: 339.232
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50450652
• Wikidata: Q82270452
• Mol file: 174021-63-7.mol

Synonyms:174021-63-7;tert-Butyl (2-(5-bromo-1H-indol-3-yl)ethyl)carbamate;[2-(5-Bromo-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester;Tert-butyl N-[2-(5-bromo-1H-indol-3-yl)ethyl]carbamate;SCHEMBL7318352;tert-Butyl(2-(5-bromo-1H-indol-3-yl)ethyl)carbamate;DTXSID50450652;LBBYTSPEGLJUIK-UHFFFAOYSA-N;MFCD22376690;AM807966;FT-0712801;F30775;A849138;t-Butyl (2-(5-bromo-1H-indol-3-yl)ethyl)carbamate;(2-(5-BroMo-1H-indol-3-yl)ethyl)carbaMic acid tert-butyl ester

Chemical Property of [2-(5-Bromo-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

• PSA: 57.61000
• LogP: 4.20200
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 338.06299
• Heavy Atom Count: 20
• Complexity: 343

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl(2-(5-bromo-1H-indol-3-yl)ethyl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCC1=CNC2=C1C=C(C=C2)Br

Technology Process of [2-(5-Bromo-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester

There total 5 articles about [2-(5-Bromo-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride (81868-12-4) → tert-butyl N-[2-(5-bromo-1H-indol-3-yl)ethyl]carbamate (174021-63-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200900033

Reference yield: 84.0%

5-bromotryptamine (3610-42-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl N-[2-(5-bromo-1H-indol-3-yl)ethyl]carbamate (174021-63-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 10 ℃; for 1h; Inert atmosphere;

Reference yield:

5-bromo-1H-indole (10075-50-0) → tert-butyl N-[2-(5-bromo-1H-indol-3-yl)ethyl]carbamate (174021-63-7)

Guidance literature:

Multi-step reaction with 4 steps

1: aluminum (III) chloride / dichloromethane / 3 h / Reflux

2: ammonium hydroxide / 4 h / 20 °C

3: lithium aluminium tetrahydride / 8 h / Reflux

4: dmap / dichloromethane / 11 h / 20 °C

With dmap; aluminum (III) chloride; ammonium hydroxide; lithium aluminium tetrahydride; In dichloromethane; 1: |Friedel-Crafts Acylation;

upstream raw materials:

di-tert-butyl dicarbonate

indole-3-glyoxylamide

5-bromotryptamine

2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride

Downstream raw materials:

C₂₂H₂₅BrN₂O₂

Refernces

• 1、 Li, Mingpeng,Xu, Yanchao,Zuo, Mingxing,Liu, Wen,Wang, Liping,Zhu, Weiming. "Semisynthetic Derivatives of Fradcarbazole A and Their Cytotoxicity against Acute Myeloid Leukemia Cell Lines". . p. 2279 - 2290. Retrieved 2019/09/19.
• 2、 Delgado, Rieardo,Blakey, Simon B.. "Cascade annulation reactions to access the structural cores of stereochemically unusual strychnos alkaloids". supporting information; experimental part. p. 1506 - 1510. Retrieved 2009/08/16.