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

Base Information

• Chemical Name: tert-Butyl 7-methyl-1H-indole-1-carboxylate
• CAS No.: 442910-62-5
• Molecular Formula: C14H17NO2
• Molecular Weight: 231.294
• Hs Code.: 2933990090
• Mol file: 442910-62-5.mol

Synonyms:tert-butyl 7-methylindole-1-carboxylate;

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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 337.278oC at 760 mmHg
• Flash Point: 157.78oC
• PSA: 31.23000
• Density: 1.064g/cm3
• LogP: 3.73290
• Storage Temp.: 2-8°C

Purity/Quality:

98%Min ^*data from raw suppliers

tert-Butyl7-Methyl-1h-indole-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

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

There total 3 articles about tert-Butyl 7-methyl-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: 98.0%

7-methyl-1H-indole (933-67-5,261352-51-6) + di-tert-butyl dicarbonate (24424-99-5) → 7-methylindole-1-carboxylic acid tert-butyl ester (442910-62-5)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 14h; Schlenk technique; Inert atmosphere;

DOI:10.1039/d1ob00430a

Reference yield: 90.0%

tert-butyl buta-2,3-dien-1-yl(3-methylfuran-2-yl)carbamate → 7-methylindole-1-carboxylic acid tert-butyl ester (442910-62-5)

Guidance literature:

In toluene; at 50 ℃; Microwave irradiation; Sealed tube;

DOI:10.1021/acs.orglett.0c00417

Reference yield: 10.0%

buta-2,3-dien-1-yl methanesulfonate (85507-12-6) + tert-butyl (3-methylfuran-2-yl)carbamate (79641-99-9) → tert-butyl buta-2,3-dien-1-yl(3-methylfuran-2-yl)carbamate + 7-methylindole-1-carboxylic acid tert-butyl ester (442910-62-5)

Guidance literature:

tert-butyl (3-methylfuran-2-yl)carbamate; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

buta-2,3-dien-1-yl methanesulfonate; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00417

upstream raw materials:

7-methyl-1H-indole

di-tert-butyl dicarbonate

buta-2,3-dien-1-yl methanesulfonate

tert-butyl (3-methylfuran-2-yl)carbamate

Downstream raw materials:

tert-butyl 7-(bromomethyl)-1H-indole-1-carboxylate

tert-butyl 7-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

tert-butyl 3-bromo-7-methylindole-1-carboxylate

Refernces

• 1、 Natho, Philipp,Yang, Zeyu,Allen, Lewis A. T.,Rey, Juliette,White, Andrew J. P.,Parsons, Philip J.. "An entry to 2-(cyclobut-1-en-1-yl)-1: H -indoles through a cyclobutenylation/deprotection cascade". supporting information. p. 4048 - 4053. Retrieved 2021/05/19.
• 2、 Jhaveri, Dishit P.,Osano, Mana,Wipf, Peter. "Formation of 6-Azaindoles by Intramolecular Diels-Alder Reaction of Oxazoles and Total Synthesis of Marinoquinoline A". supporting information. p. 2215 - 2219. Retrieved 2020/04/09.