1-tert-butyl 2-ethyl 5-methyl-1H-indole-1,2-dicarboxylate

Base Information

• Chemical Name: 1-tert-butyl 2-ethyl 5-methyl-1H-indole-1,2-dicarboxylate
• CAS No.: 1233086-44-6
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358
• Hs Code.: 2933990090
• Mol file: 1233086-44-6.mol

Synonyms:1-tert-butyl 2-ethyl 5-methyl-1H-indole-1,2-dicarboxylate

Chemical Property of 1-tert-butyl 2-ethyl 5-methyl-1H-indole-1,2-dicarboxylate

Chemical Property:

• PSA: 57.53000
• Density: 1.12±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 3.90960
• Storage Temp.: 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

1-tert-Butyl2-ethyl5-methyl-1H-indole-1,2-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-tert-butyl 2-ethyl 5-methyl-1H-indole-1,2-dicarboxylate

There total 1 articles about 1-tert-butyl 2-ethyl 5-methyl-1H-indole-1,2-dicarboxylate 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:

5-methyl-1H-indole-2-carboxylic acid ethyl ester (16382-15-3) + di-tert-butyl dicarbonate (24424-99-5) → C17H21NO4 (1233086-44-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

Reference yield:

C17H21NO4 (1233086-44-6) → benzyl 5-((diethoxyphosphoryl)methyl)-1H-indole-2-carboxylate (1233086-47-9)

Guidance literature:

Multi-step reaction with 3 steps

1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 12 h / Reflux; Inert atmosphere

2: 12 h / 100 °C / Inert atmosphere

3: titanium(IV) isopropylate / 12 h / 100 °C / Inert atmosphere

With titanium(IV) isopropylate; N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;

DOI:10.1021/acs.jmedchem.9b01530

Reference yield:

C17H21NO4 (1233086-44-6) → C44H52F2N7O9P

Guidance literature:

Multi-step reaction with 7 steps

1.1: dibenzoyl peroxide; N-Bromosuccinimide / tetrachloromethane / 12 h / Reflux; Inert atmosphere

2.1: 12 h / 100 °C / Inert atmosphere

3.1: titanium(IV) isopropylate / 12 h / 100 °C / Inert atmosphere

4.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

4.2: 12 h / 0 - 20 °C / Inert atmosphere

5.1: N-fluorobis(benzenesulfon)imide; sodium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

6.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 12 h / 20 °C / 760.05 Torr

7.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; N-Bromosuccinimide; palladium 10% on activated carbon; hydrogen; sodium hexamethyldisilazane; sodium hydride; N-fluorobis(benzenesulfon)imide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.9b01530

upstream raw materials:

5-methyl-1H-indole-2-carboxylic acid ethyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

benzyl 5-((diethoxyphosphoryl)methyl)-1H-indole-2-carboxylate

Refernces

• 1、 -. "SMALL MOLECULE DEGRADERS OF STAT3". Paragraph 1345. . Retrieved 2020/10/20.
• 2、 Zhou, Haibin,Bai, Longchuan,Xu, Renqi,Zhao, Yujun,Chen, Jianyong,McEachern, Donna,Chinnaswamy, Krishnapriya,Wen, Bo,Dai, Lipeng,Kumar, Praveen,Yang, Chao-Yie,Liu, Zhaomin,Wang, Mi,Liu, Liu,Meagher, Jennifer L.,Yi, Han,Sun, Duxin,Stuckey, Jeanne A.,Wang, Shaomeng. "Structure-Based Discovery of SD-36 as a Potent, Selective, and Efficacious PROTAC Degrader of STAT3 Protein". . p. 11280 - 11300. Retrieved 2019/12/27.