5-(TERT-BUTYLDIMETHYLSILYLOXY)-1H-INDOLE-2-BORONIC ACID, N-BOC PROTECTED 98

Base Information

• Chemical Name: 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1H-INDOLE-2-BORONIC ACID, N-BOC PROTECTED 98
• CAS No.: 335649-61-1
• Molecular Formula: C19H30BNO5Si
• Molecular Weight: 391.347
• Hs Code.: 2933990090
• Mol file: 335649-61-1.mol

Synonyms:[1-(tert-Butoxycarbonyl)-5-[(tert-butyldimethylsilyl)oxy]-1H-indol-2-yl]boronicacid;[5-(tert-Butyldimethylsilanoxy)-1-(tert-butoxycarbonyl)-1H-indol-2-yl]boronicacid;

Chemical Property of 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1H-INDOLE-2-BORONIC ACID, N-BOC PROTECTED 98

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 104-106
• Refractive Index: 1.503
• Boiling Point: 486.721 °C at 760 mmHg
• PKA: 8.01±0.30(Predicted)
• Flash Point: 248.16 °C
• PSA: 80.92000
• Density: 1.072 g/cm³
• LogP: 3.48830
• Storage Temp.: Keep Cold

Purity/Quality:

98%min ^*data from raw suppliers

1-BOC-5-TBDMSO-indole-2-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1H-INDOLE-2-BORONIC ACID, N-BOC PROTECTED 98

There total 3 articles about 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1H-INDOLE-2-BORONIC ACID, N-BOC PROTECTED 98 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: 95.0%

5-(tert-butyl-dimethyl-silanyloxy)-indole-1-carboxylic acid tert-butyl ester → {1-[(tert-butoxy)carbonyl]-5-[(tert-butyldimethylsilyl)oxy]-1H-indol-2-yl}boronic acid (335649-61-1)

Guidance literature:

5-(tert-butyl-dimethyl-silanyloxy)-indole-1-carboxylic acid tert-butyl ester; With Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at 0 ℃; for 1h;

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

DOI:10.1021/ja1112996

Reference yield:

5-(tert-butyl-dimethyl-silanyloxy)-indole-1-carboxylic acid tert-butyl ester + Trimethyl borate (121-43-7,63156-11-6) → {1-[(tert-butoxy)carbonyl]-5-[(tert-butyldimethylsilyl)oxy]-1H-indol-2-yl}boronic acid (335649-61-1)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; pentane;

Reference yield:

→ {1-[(tert-butoxy)carbonyl]-5-[(tert-butyldimethylsilyl)oxy]-1H-indol-2-yl}boronic acid (335649-61-1)

Guidance literature:

upstream raw materials:

Trimethyl borate

Downstream raw materials:

5-(tert-butyl-dimethyl-silanyloxy)-2-(3-chloro-benzyl)-indole-1-carboxylic acid tert-butyl ester

C₃₀H₄₂N₆O₄Si

5-benzyloxy-3-[1-tert-butoxycarbonyl-5-(tert-butyl-dimethylsilanyloxy)-1H-indol-2-yl]indazole-1-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "JAK INHIBITOR". Page/Page column 82. . Retrieved 2009/10/21.
• 2、 -. "Tyrosine kinase inhibitors". . . Retrieved 2008/06/13.