1H-Indole-1,6-dicarboxylic acid, 2-borono-, 1-(1,1-dimethylethyl) 6-methyl ester (9CI)

Base Information

• Chemical Name: 1H-Indole-1,6-dicarboxylic acid, 2-borono-, 1-(1,1-dimethylethyl) 6-methyl ester (9CI)
• CAS No.: 848357-46-0
• Molecular Formula: C15H18 B N O6
• Molecular Weight: 319.12
• Hs Code.: 2933990090
• Mol file: 848357-46-0.mol

Synonyms:[6-Methoxycarbonyl-1-(tert-butoxycarbonyl)-1H-indol-2-yl]boronicacid

Chemical Property of 1H-Indole-1,6-dicarboxylic acid, 2-borono-, 1-(1,1-dimethylethyl) 6-methyl ester (9CI)

Chemical Property:

• Vapor Pressure: 7.01E-11mmHg at 25°C
• Refractive Index: 1.546
• Boiling Point: 501.6°C at 760 mmHg
• Flash Point: 257.1°C
• PSA: 97.99000
• Density: 1.24g/cm³
• LogP: 0.89090
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-BOC-6-(methoxycarbonyl)indole-2-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Indole-1,6-dicarboxylic acid, 2-borono-, 1-(1,1-dimethylethyl) 6-methyl ester (9CI)

There total 4 articles about 1H-Indole-1,6-dicarboxylic acid, 2-borono-, 1-(1,1-dimethylethyl) 6-methyl ester (9CI) 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: 75.6%

indole-1,6-dicarboxylic acid 1-tert-butyl ester 6-methyl ester (354587-63-6) → 6-carbocxylic acid methyl ester-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid (848357-46-0)

Guidance literature:

indole-1,6-dicarboxylic acid 1-tert-butyl ester 6-methyl ester; With Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at 0 ℃; for 2.16667h;

With hydrogenchloride; In tetrahydrofuran; n-heptane; ethylbenzene; water; at 0 ℃; for 0.0833333h; pH=4;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 6-carbocxylic acid methyl ester-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid (848357-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap / tetrahydrofuran / 2 h / 20 °C

2.1: lithium diisopropyl amide; Triisopropyl borate / hexane; tetrahydrofuran / 2.5 h / -5 °C

2.2: Cooling with ice

With Triisopropyl borate; lithium diisopropyl amide; dmap; In tetrahydrofuran; hexane;

Reference yield:

Indole-6-carboxylic acid (1670-82-2,261352-47-0) → 6-carbocxylic acid methyl ester-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid (848357-46-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C

1.2: 2 h / 20 °C

2.1: dmap / tetrahydrofuran / 2 h / 20 °C

3.1: lithium diisopropyl amide; Triisopropyl borate / hexane; tetrahydrofuran / 2.5 h / -5 °C

3.2: Cooling with ice

With Triisopropyl borate; potassium carbonate; lithium diisopropyl amide; dmap; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

upstream raw materials:

indole-1,6-dicarboxylic acid 1-tert-butyl ester 6-methyl ester

di-tert-butyl dicarbonate

Indole-6-carboxylic acid

indole-6-carboxylic acid methyl ester

Downstream raw materials:

benzyl (2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)carbamate

benzyl N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylcarbamate

benzyl N-{2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl}-N-methylcarbamate

2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylic acid [2-(tert-butyldiphenylsilyloxy)-1-methylethyl]amide

Refernces

• 1、 -. "THIENOPYRAZOLES". Page/Page column 85-86. . Retrieved 2008/06/13.