ChemicalBook CAS DataBase List 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

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 synthesis

9synthesis methods

Product 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 Number:1242156-76-8
Molecular formula:C27H32BFN2O5
Molecular Weight:494.36

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

1242157-24-9
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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
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$713.00/100mg

Yield:1242156-76-8 81%

Reaction Conditions:

Stage #1: 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzyl acetate;bis(pinacol)diboranewith potassium acetate;XPhos in 1,4-dioxane; for 0.25 h;Inert atmosphere of argon;
Stage #2: bis(dibenzylideneacetone)-palladium⁽⁰⁾ in 1,4-dioxane at 60; for 18 h;

Steps:

26

In a microwave reaction vial, added ccetic acid 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-chloro-benzyl ester (329 mg, 0.818 mmol), bis-pinaco-diboron (416 mg, 1.637 mmol), KOAc (241 mg, 2.454 mmol) and Xphos (39 mg, 0.0818 mmol) and dioxane (4 mL). Bubble argon through for 15 min and then add Pd(dba)2 (24 mg, 0.0409 mmol). Seal the tube and heat it to 60° C. for 18 hrs. The reaction mixture was then diluted with EtOAc (5 mL) and washed with NaHCO₃ (concentrated) (1*10 mL) and water (10 mL). The organic phase was then concentrated and purified on silica gel column with 25% EtOAc in Hex to give 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 as an yellow oil (330 mg, 81%).

References:

US2010/222325,2010,A1 Location in patent:Page/Page column 69

1413063-73-6 Synthesis