3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

Base Information

• Chemical Name: 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• CAS No.: 847448-73-1
• Molecular Formula: C15H17NO4
• Molecular Weight: 275.304
• Hs Code.: 2933990090
• Mol file: 847448-73-1.mol

Synonyms:tert-Butyl 3-formyl-6-methoxy-1H-indole-1-carboxylate;1-Boc-3-formyl-6-methoxyindole;

Chemical Property of 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.543
• Boiling Point: 415.487 °C at 760 mmHg
• Flash Point: 205.079 °C
• PSA: 57.53000
• Density: 1.16 g/cm³
• LogP: 3.24560

Purity/Quality:

99% ^*data from raw suppliers

3-Formyl-6-methoxyindole-1-carboxylicacidtert-butylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER

There total 2 articles about 3-FORMYL-6-METHOXYINDOLE-1-CARBOXYLIC 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: 97.0%

6-methoxy-1H-indole-3-carbaldehyde (70555-46-3) + di-tert-butyl dicarbonate (24424-99-5) → 6-methoxy-1-(tert-butoxycarbonyl)indole-3-carboxaldehyde (847448-73-1)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃;

DOI:10.1055/s-2004-834905

Reference yield:

6-methoxylindole (3189-13-7) → 6-methoxy-1-(tert-butoxycarbonyl)indole-3-carboxaldehyde (847448-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1: trichlorophosphate / 2 h / 0 - 20 °C / Inert atmosphere

2: dmap / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

With dmap; trichlorophosphate; In tetrahydrofuran;

DOI:10.1002/anie.202102416

Reference yield: 72.0%

1,3-dibenzylimidazolidine-2,4-dione (16935-43-6) + 6-methoxy-1-(tert-butoxycarbonyl)indole-3-carboxaldehyde (847448-73-1) → tert-butyl 3-((1,3-dibenzyl-2,5-dioxoimidazolidin-4-yl)(hydroxy)methyl)-6-methoxy-1H-indole-1-carboxylate

Guidance literature:

1,3-dibenzylimidazolidine-2,4-dione; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

6-methoxy-1-(tert-butoxycarbonyl)indole-3-carboxaldehyde; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.202100184

upstream raw materials:

6-methoxy-1H-indole-3-carbaldehyde

di-tert-butyl dicarbonate

6-methoxylindole

Downstream raw materials:

1-(6-methoxy-1H-indol-3-yl)-2-((2-methoxypyridin-4-yl)amino)-2-phenylethanone

1-(6-methoxy-1H-indol-3-yl)-2-((3-methoxyphenyl)amino)-2-phenylethanone

C₁₅H₁₉NO₄

Refernces

• 1、 He, Ling,Jiang, Yan,Qiao, Zhen,Qiu, Hanyue,Su, Xiaojiao,Tan, Qiuyuan,Yang, Jiaojiao,Yang, Zhao,Zhang, Min,Zhou, Wenqiang. "Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids". supporting information. p. 13105 - 13111. Retrieved 2021/05/10.
• 2、 Markey, Sophie J.,Lewis, William,Moody, Christopher J.. "A new route to α-carbolines based on 6π-electrocyclization of indole-3-alkenyl oximes". supporting information. p. 6306 - 6308. Retrieved 2014/01/17.