2(1H)-ISOQUINOLINECARBOXYLIC ACID, 3,4-DIHYDRO-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, 1,1-DIMETHYLETHYL ESTER

Base Information

• Chemical Name: 2(1H)-ISOQUINOLINECARBOXYLIC ACID, 3,4-DIHYDRO-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, 1,1-DIMETHYLETHYL ESTER
• CAS No.: 937048-76-5
• Molecular Formula: C20H30BNO4
• Molecular Weight: 359.273
• Mol file: 937048-76-5.mol

Synonyms:2(1H)-ISOQUINOLINECARBOXYLIC ACID, 3,4-DIHYDRO-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, 1,1-DIMETHYLETHYL ESTER;tert-Butyl 7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate;2-Boc-3,4-dihydro-1H-isoquinoline-7-boronic acid pinacol ester;7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Chemical Property of 2(1H)-ISOQUINOLINECARBOXYLIC ACID, 3,4-DIHYDRO-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, 1,1-DIMETHYLETHYL ESTER

Chemical Property:

• Boiling Point: 462.2±45.0 °C (760 mmHg)
• PSA: 48.00000
• Density: 1.10±0.1 g/cm3 (20 °C, 760 mmHg)
• LogP: 3.21690
• Storage Temp.: 2-8°C

Purity/Quality:

97% purity ^*data from raw suppliers

7-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylicAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 7-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid tert-Butyl Ester is a reactant in the synthesis of tyrosine kinase inhibitors in the treatment of proliferative diseases.

Technology Process of 2(1H)-ISOQUINOLINECARBOXYLIC ACID, 3,4-DIHYDRO-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, 1,1-DIMETHYLETHYL ESTER

There total 6 articles about 2(1H)-ISOQUINOLINECARBOXYLIC ACID, 3,4-DIHYDRO-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-, 1,1-DIMETHYLETHYL 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: 96.0%

7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylic acid tert-butyl ester (258515-65-0) + bis(pinacol)diborane (73183-34-3) → 7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (937048-76-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 90 ℃; Inert atmosphere;

DOI:10.3390/molecules24234302

Reference yield: 74.0%

7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylic acid tert-butyl ester (258515-65-0) → 7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (937048-76-5)

Guidance literature:

With potassium acetate; bis(pinacol)diborane; In 1,4-dioxane; at 100 ℃; for 16h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (937048-76-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium carbonate / tetrahydrofuran; water / 20 °C

2: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; sodium carbonate; In tetrahydrofuran; water; dimethyl sulfoxide;

upstream raw materials:

7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylic acid tert-butyl ester

bis(pinacol)diborane

7-bromo-1,2,3,4-tetrahydroisoquinoline

di-tert-butyl dicarbonate

Downstream raw materials:

(R)-5-(2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1,2,3,4-tetrahydroisoquinoline-7-yl)pyridin-2-amine

7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

{2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}boronic acid

Refernces

• 1、 -. "MACROCYCLIC COMPOUND AND USE THEREOF". Paragraph 0193. . Retrieved 2020/07/05.
• 2、 -. "DIHYDROISOQUINOLINE-2(1H)-CARBOXAMIDE AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS". Paragraph 000570. . Retrieved 2019/11/04.