1H-Indole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) ester

Base Information

• Chemical Name: 1H-Indole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) ester
• CAS No.: 188751-54-4
• Molecular Formula: C14H15NO4
• Molecular Weight: 261.27300
• Hs Code.: 2933990090
• Mol file: 188751-54-4.mol

Synonyms:N-Boc-indole-5-carboxylic acid;1-Boc-1H-indole-5-carboxylic acid;

Chemical Property of 1H-Indole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) ester

Chemical Property:

• PSA: 68.53000
• LogP: 3.12270
• Storage Temp.: 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

1-(tert-Butoxycarbonyl)-1H-indole-5-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Indole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) ester

There total 1 articles about 1H-Indole-1,5-dicarboxylic acid, 1-(1,1-dimethylethyl) 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: 54.0%

carbon dioxide (124-38-9,18923-20-1) + 5-bromo-indole-1-carboxylic acid tert-butyl ester (182344-70-3) → 1-(tert-butoxycarbonyl)-1H-indole-5-carboxylic acid (188751-54-4)

Guidance literature:

carbon dioxide; With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate; In 1,4-dioxane; at 65 ℃; for 0.333333h; Schlenk technique;

5-bromo-indole-1-carboxylic acid tert-butyl ester; With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; toluene; at 100 ℃; for 12h; Schlenk technique; Sealed tube;

DOI:10.1039/c8cc06820h

Reference yield:

1-(tert-butoxycarbonyl)-1H-indole-5-carboxylic acid (188751-54-4) + diazomethyl-trimethyl-silane (18107-18-1) → 1-tert-butoxycarbonyl-5-methoxycarbonylindole (272438-11-6)

Guidance literature:

In methanol; diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/jacs.7b04838

Reference yield:

1-(tert-butoxycarbonyl)-1H-indole-5-carboxylic acid (188751-54-4) → 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (777061-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexyl-carbodiimide / ethyl acetate / 3 h / 20 °C / Inert atmosphere

2: pyridine; caesium carbonate / ethyl acetate / 30 h / 35 °C / Inert atmosphere; Irradiation

With pyridine; caesium carbonate; dicyclohexyl-carbodiimide; In ethyl acetate;

DOI:10.1021/jacs.7b03127

upstream raw materials:

carbon dioxide

5-bromo-indole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

1-tert-butoxycarbonyl-5-methoxycarbonylindole

Refernces

• 1、 Paridala, Kumaraswamy,Lu, Sheng-Mei,Wang, Meng-Meng,Li, Can. "Tandem one-pot CO2 reduction by PMHS and silyloxycarbonylation of aryl/vinyl halides to access carboxylic acids". supporting information. p. 11574 - 11577. Retrieved 2018/10/31.