TERT-BUTYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE

Base Information

• Chemical Name: TERT-BUTYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
• CAS No.: 893566-72-8
• Molecular Formula: C20H30 B N O4
• Molecular Weight: 359.273
• Hs Code.: 2934999090
• Mol file: 893566-72-8.mol

Synonyms:6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylicacid tert-butyl ester; tert-Butyl6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property of TERT-BUTYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE

Chemical Property:

• Vapor Pressure: 1.01E-08mmHg at 25°C
• Refractive Index: 1.527
• Boiling Point: 462.2°C at 760 mmHg
• Flash Point: 233.3°C
• PSA: 48.00000
• Density: 1.1g/cm³
• LogP: 3.21690
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98%min ^*data from raw suppliers

tert-?Butyl6-?(4,?4,?5,?5-?tetramethyl-?1,?3,?2-?dioxaborolan-?2-?yl)?-?3,?4-?dihydroisoquinoline-?2(1H)?-?carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-?Butyl 6-?(4,?4,?5,?5-?tetramethyl-?1,?3,?2-?dioxaborolan-?2-?yl)?-?3,?4-?dihydroisoquinoline-?2(1H)?-?carboxylate is a reactant in the synthesis of tyrosine kinase inhibitors in the treatment of proliferative diseases.

Technology Process of TERT-BUTYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE

There total 13 articles about TERT-BUTYL 6-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE 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: 90.12%

6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline (893566-74-0) + bis(pinacol)diborane (73183-34-3) → 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (893566-72-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In dimethyl sulfoxide; at 65 ℃; for 2h; Inert atmosphere;

Reference yield:

tert-butyl 8-bromo-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (893566-75-1) + 6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline (893566-74-0) + bis(pinacol)diborane (73183-34-3) → 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (893566-72-8) + tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (893566-73-9)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 85 ℃; for 4h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (893566-72-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / methanol / 20 °C / Inert atmosphere

2.1: 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.08 h / 20 °C / Inert atmosphere

2.2: 4 h / 90 °C / Inert atmosphere

With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; methanol;

upstream raw materials:

tert-butyl 8-bromo-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline

bis(pinacol)diborane

6-trifluoromethanesulfonyloxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Downstream raw materials:

2-[(1-methylethyl)oxy]-5-[5-(1,2,3,4-tetrahydro-6-isoquinolinyl)-1,3,4-thiadiazol-2-yl]benzonitrile

3-[6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)-isoquinolinyl]propanamide

Refernces

• 1、 -. "COMPOUNDS FOR TREATMENT OF PD-L1 DISEASES". Paragraph 0132; 0134. . Retrieved 2021/01/21.
• 2、 -. "IMIDAZO[1,2-C]PYRIMIDINE DERIVATIVES AS PRC2 INHIBITORS FOR TREATING CANCER". Paragraph 0328-0329. . Retrieved 2020/12/29.