tert-Butyl 7-chloro-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 7-chloro-1H-indole-1-carboxylate
• CAS No.: 1004558-41-1
• Molecular Formula: C13H14ClNO2
• Molecular Weight: 251.713
• DSSTox Substance ID: DTXSID30682075
• Nikkaji Number: J2.863.385H
• Wikidata: Q82606336
• Mol file: 1004558-41-1.mol

Synonyms:1004558-41-1;tert-Butyl 7-chloro-1H-indole-1-carboxylate;1-BOC 7-Chloroindole;tert-butyl 7-chloroindole-1-carboxylate;SCHEMBL2877952;DTXSID30682075;DKEVEWZLEMGFNK-UHFFFAOYSA-N;MFCD13183456;AKOS015837037;BS-19039;tert-Butyl7-chloro-1H-indole-1-carboxylate;1-(tert-Butoxycarbonyl)-7-chloro-1H-indole;FT-0706817;7-chloro-indole-1-carboxylic acid tert-butyl ester

Chemical Property of tert-Butyl 7-chloro-1H-indole-1-carboxylate

Chemical Property:

• PSA: 31.23000
• LogP: 4.07790
• Storage Temp.: Room temperature.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 251.0713064
• Heavy Atom Count: 17
• Complexity: 300

Purity/Quality:

97% ^*data from raw suppliers

1-BOC7-Chloroindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CC2=C1C(=CC=C2)Cl

Technology Process of tert-Butyl 7-chloro-1H-indole-1-carboxylate

There total 6 articles about tert-Butyl 7-chloro-1H-indole-1-carboxylate 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: 94.0%

7-chloro-1H-indole (53924-05-3) + di-tert-butyl dicarbonate (24424-99-5) → 7-chloroindole-1-carboxylic acid tert-butyl ester (1004558-41-1)

Guidance literature:

With dmap; triethylamine; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; at 20 ℃; for 11h;

DOI:10.1002/anie.200901072

Reference yield: 68.0%

tert-butyl carbazate (4248-19-5) + 1-bromo-2-[2-bromovinyl]-6-chlorobenzene → 7-chloroindole-1-carboxylic acid tert-butyl ester (1004558-41-1)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; In toluene; at 110 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tet.2010.05.046

Reference yield:

chloro-trimethyl-silane (75-77-4) + N-tert-butoxycarbonyl-7-chloro-2,3-dihydroindole (143262-18-4) → 7-chloroindole-1-carboxylic acid tert-butyl ester (1004558-41-1) + 7-Chloro-2-trimethylsilanyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) Et2O, cyclohexane, -78 deg C, 1 h, 2.) -78 deg C, 0.5 h; -78 deg C -> room temperature; room temperature, overnight;

DOI:10.1021/jo9708856

upstream raw materials:

chloro-trimethyl-silane

N-tert-butoxycarbonyl-7-chloro-2,3-dihydroindole

allyl bromide

methyl iodide

Downstream raw materials:

[1-(tert-butoxycarbonyl)-7-chloro-H-indol-2-yl]boronic acid