1-Boc-3,4-Dibromoindole

Base Information

• Chemical Name: 1-Boc-3,4-Dibromoindole
• CAS No.: 219943-38-1
• Molecular Formula: C13H13Br2NO2
• Molecular Weight: 375.06
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10444890
• Nikkaji Number: J1.742.418A
• Wikidata: Q82263165
• Mol file: 219943-38-1.mol

Synonyms:1-Boc-3,4-Dibromoindole;219943-38-1;Tert-butyl 3,4-dibromoindole-1-carboxylate;3,4-DIBROMOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;tert-butyl 3,4-dibromo-1H-indole-1-carboxylate;3,4-Dibromo-1H-indole-1-carboxylic acid tert-butyl ester;DTXSID10444890;FT-0723233

Chemical Property of 1-Boc-3,4-Dibromoindole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.608
• Boiling Point: 414.518 °C at 760 mmHg
• Flash Point: 204.494 °C
• PSA: 31.23000
• Density: 1.64g/cm³
• LogP: 4.94950
• Storage Temp.: 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 374.92925
• Heavy Atom Count: 18
• Complexity: 329

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dibromoindole-1-carboxylic acid tert-butyl ester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=C(C2=C1C=CC=C2Br)Br

Technology Process of 1-Boc-3,4-Dibromoindole

There total 5 articles about 1-Boc-3,4-Dibromoindole 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:

di-tert-butyl dicarbonate (24424-99-5) + 3,4-dibromo-1H-indole (219943-37-0) → 3,4-Dibromo-indole-1-carboxylic acid tert-butyl ester (219943-38-1)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; for 14h; Yield given;

DOI:10.1021/jo981723s

Reference yield:

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine (146886-51-3) → 3,4-Dibromo-indole-1-carboxylic acid tert-butyl ester (219943-38-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: t-BuLi / diethyl ether; pentane / 1 h / 0 °C

1.2: 56 percent / BrCH₂CH₂Br

2.1: 84 percent / NBS / CH₂Cl₂; methanol / 0.03 h / 20 °C

3.1: TBAF / tetrahydrofuran / 0.17 h / 20 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; N-Bromosuccinimide; tetrabutyl ammonium fluoride; tert.-butyl lithium; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane; 2.1: retro-Mannich fragmentation;

DOI:10.1021/ol017310m

Reference yield:

(4-bromo-1-triisopropylsilyl-1H-indol-3-ylmethyl)-dimethylamine (146886-59-1) → 3,4-Dibromo-indole-1-carboxylic acid tert-butyl ester (219943-38-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / NBS / CH₂Cl₂; methanol / 0.03 h / 20 °C

2: TBAF / tetrahydrofuran / 0.17 h / 20 °C

3: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; N-Bromosuccinimide; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1: retro-Mannich fragmentation;

DOI:10.1021/ol017310m

upstream raw materials:

di-tert-butyl dicarbonate

3,4-dibromo-1H-indole

1-(N-triisopropylsilyl-1H-indol-3-yl)-N,N-dimethylmethanamine

(4-bromo-1-triisopropylsilyl-1H-indol-3-ylmethyl)-dimethylamine

Downstream raw materials:

(R)-4-bromo-α-N-trityltryptophan methyl ester

(R)-4-bromo-α-N-trityltryptophan

(R)-4-bromotryptophan

(R)-4-bromo-α-N-trityltryptophan trityl ester

Refernces

• 1、 Hurt, Clarence R.,Lin, Ronghui,Rapoport, Henry. "Enantiospecific synthesis of (r)-4-amino-5-oxo-1,3,4,5- tetrahydrobenz[cd]indole, an advanced intermediate containing the tricyclic core of the ergots". . p. 225 - 233. Retrieved 2007/10/03.