1H-Indazole, 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- synthesis
- Product Name:1H-Indazole, 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
- CAS Number:1613639-49-8
- Molecular formula:C13H16BClN2O2
- Molecular Weight:278.54
73183-34-3
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Yield:1613639-49-8 420 mg
Reaction Conditions:
with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane at 90;Inert atmosphere;
Steps:
28.1 Preparation of 3-chloro-5-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH- indazole
Under an Ar atmosphere, a mixture of 5-bromo-3-chloro-lH-indazo (1 g, 4.3 mmol), bis(pinacolato)diboron (2.2 g, 8.7 mmol), [l,l '-bis(diphenylphosphino)ferrocene]- dichloropalladium(II) (700 mg) and potassium acetate (1.26 g, 12.9 mmol) in 1,4-dioxane (12 mL) was heated at 90 °C overnight. The residue was partitioned between EtOAc and brine. The aqueous layer was separated and extracted with EtOAc. The combined organic layers were concentrated and the residue was purified by column chromatography to afford 3-chloro-5- (4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-indazole (420 mg) which was directly used in the next step.
References:
WO2014/90692,2014,A1 Location in patent:Page/Page column 58; 59
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