2-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate

Base Information

• Chemical Name: 2-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate
• CAS No.: 1242156-76-8
• Molecular Formula: C27H32BFN2O5
• Molecular Weight: 494.371
• Hs Code.: 2933998090
• Mol file: 1242156-76-8.mol

Synonyms:2-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate;Acetic acid 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)benzyl ester

Chemical Property of 2-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate

Chemical Property:

• PSA: 79.65000
• LogP: 4.18460

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-(6-(tert-Butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylacetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate

There total 9 articles about 2-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate 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: 81.0%

2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzyl acetate (1242157-24-9) + bis(pinacol)diborane (73183-34-3) → 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (1242156-76-8)

Guidance literature:

2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzyl acetate; bis(pinacol)diborane; With potassium acetate; XPhos; In 1,4-dioxane; for 0.25h; Inert atmosphere of argon;

bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; at 60 ℃; for 18h;

Reference yield: 75.0%

acetic acid 2-bromo-6-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-benzyl ester (1413063-73-6) + bis(pinacol)diborane (73183-34-3) → 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (1242156-76-8)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80 ℃; for 24h; Inert atmosphere;

Reference yield:

2,6-dibromotoluene (69321-60-4) → 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate (1242156-76-8)

Guidance literature:

Multi-step reaction with 4 steps

1: N-Bromosuccinimide / dibenzoyl peroxide / tetrachloromethane / 20 h / Reflux

2: N,N-dimethyl-formamide / 6 h / 105 °C

3: caesium carbonate / copper(l) iodide; N,N-dimethylethylenediamine / N,N-dimethyl-formamide / 4 h / 150 °C / Inert atmosphere

4: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 24 h / 80 °C / Inert atmosphere

With N-Bromosuccinimide; potassium acetate; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; N,N-dimethylethylenediamine; dibenzoyl peroxide; In tetrachloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzyl acetate

bis(pinacol)diborane

acetic acid 2-bromo-6-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-benzyl ester

2,6-dibromotoluene

Downstream raw materials:

acetic acid 2-(5-{tert-butoxycarbonyl-[5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amino}-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-benzyl ester

6-tert-Butyl-8-fluoro-2-(2-hydroxymethyl-3-{1-methyl-5-[5-(1-methyl-azetidin-3-yloxy)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-2H-phthalazin-1-one

6-tert-Butyl-8-fluoro-2-(2-hydroxymethyl-3-{5-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl}-phenyl)-2H-phthalazin-1-one

Acetic acid 2-{5-[5-(1-amino-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl}-6-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-benzyl ester

Refernces

• 1、 -. "Inhibitors of Bruton's Tyrosine Kinase". Page/Page column 50-51. . Retrieved 2012/03/08.
• 2、 -. "Inhibitors of Bruton's Tyrosine Kinase". Page/Page column 69. . Retrieved 2010/09/07.