ChemicalBook CAS DataBase List 2-AMINO-4-CHLOROPHENYL BORONIC ACID PINACOL ESTER

2-AMINO-4-CHLOROPHENYL BORONIC ACID PINACOL ESTER synthesis

8synthesis methods

Product Name:2-AMINO-4-CHLOROPHENYL BORONIC ACID PINACOL ESTER
CAS Number:863578-21-6
Molecular formula:C12H17BClNO2
Molecular Weight:253.53

823-57-4 Synthesis

823-57-4
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2-AMINO-4-CHLOROPHENYL BORONIC ACID PINACOL ESTER

863578-21-6
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$28.00/100mg

Yield: 96%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂;potassium acetate;bis(pinacol)diborane in dimethyl sulfoxide at 85;Inert atmosphere;

Steps:

14.3 Step 3: Synthesis of 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
To a round bottomed flask was added PdCl2(dppf)-CH2Cl2 adduct (1.347 g, 1.650 mmol), KOAc (6.48 g, 66.0 mmol), bis(pinacolato)diboron (12.57 g, 49.5 mmol), 2- bromo-5-chloroaniline (6.81 g, 33 mmol), and DMSO (100 mL). The solution was evacuated/backfilled with N2 (3x) before heating to 85 °C overnight. The solution was cooled to room temperature and diluted with MTBE and water. The solution was filtered and the layers were separated. The aqueous phase was extracted with MTBE and the combined organics layer was washed with water, brine, dried over Na2504, filtered, and concentrated. The crude residue was purified via Biotage to afford 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)aniline (8.06 g, 31.8 mmol, 96% yield). m/z (ESI) 254 [M+H]⁺

References:

CONSTELLATION PHARMACEUTICALS, INC.;ALBRECHT, Brian, K.;GEHLING, Victor, S.;TAYLOR, Alexander, M.;VASWANI, Rishi, G. WO2013/184878, 2013, A1 Location in patent:Paragraph 00183; 00184

823-57-4 Synthesis

823-57-4
176 suppliers
$6.00/1g