ChemicalBook CAS DataBase List 1-[4-(4.4.5.5-tetramethyl-[1.3.2]dioxaborolan-2-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid methyl ester

1-[4-(4.4.5.5-tetramethyl-[1.3.2]dioxaborolan-2-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid methyl ester synthesis

7synthesis methods

Product Name:1-[4-(4.4.5.5-tetramethyl-[1.3.2]dioxaborolan-2-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid methyl ester
CAS Number:1423700-75-7
Molecular formula:C23H27BO4
Molecular Weight:378.27

methyl 1-[4-(4-bromophenyl)phenyl]cyclopropanecarboxylate

1423700-73-5
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1-[4-(4.4.5.5-tetramethyl-[1.3.2]dioxaborolan-2-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid methyl ester

1423700-75-7
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Yield:1423700-75-7 76%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane;Reflux;Inert atmosphere;

Steps:

XVII

To a solution of compound XVII-3 (440 mg, 1.33mmol) in dioxane (20 mL) was added KOAc (260 mg, 2.66 mmol), compound XVII-13 (676 mg, 2.66 mmol), Pd(dppf)Cl₂ (97 mg, 0.13 mmol). The mixture was purged with nitrogen and the mixture was heated at reflux overnight. After being cooled to rt, the mixture was concentrated, diluted with water (40 mL), and extracted with EtOAc (100 mL><3). The combined organic layer was washed with brine, dried over anhydrous Na₂S0₄, and concentrated in vacuo. The residue was purified by prep-TLC (PE:EA=3: 1) to give compound XVII-4 (380 mg, yield 76%) as pale-yellow solid. MS (ESI) m/z (M+H)⁺ 378.9.

References:

WO2013/25733,2013,A1 Location in patent:Paragraph 0499

638220-35-6 Synthesis