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ChemicalBook CAS DataBase List 5-cyanobenzo[b]thiophen-2-ylboronic acid
1142946-81-3

5-cyanobenzo[b]thiophen-2-ylboronic acid synthesis

4synthesis methods
-

Yield:1142946-81-3 40.9 %

Reaction Conditions:

Stage #1: benzo[b]thiophene-5-carbonitrilewith n-butyllithium in tetrahydrofuran;pentane at -78;
Stage #2: Trimethyl borate in tetrahydrofuran;pentane at -78 - 20;

Steps:

5 (Synthesis of Intermediate (12))

To a solution of 2.3 g (14.5 mmol) of intermediate (11) in 83 mL of anhydrous THF, 10.2 mL (17.3 mmol, 1.7 M in pentane) of n-BuLi was slowly added dropwise at -78 °C and stirred for 15 minutes.After slowly adding 43.0 mL (385.7 mmol) of trimethylborate dropwise, the mixture was stirred at -78°C for 15 minutes and then stirred at room temperature for 2 hours.After confirming the completion of the reaction, 1M HCl aqueous solution was slowly added dropwise and concentrated. Distilled water was added to the concentrate and extracted with ethyl acetate.The separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by column chromatography (MeOH/CHCl3) to obtain 1.2 g (yield: 40.9%) of the compound (Intermediate (12)) as an off-white solid.

References:

WO2023/18040,2023,A1 Location in patent:Paragraph 356-357; 360-361