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2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
12.6 g
at 20.0℃; for 24.0h;Molecular sieve;
A suspension of 10.0 g (55.1 mmol) of <strong>[871332-95-5](4-chloro-3-cyanophenyl)boronic acid</strong>, 6.52 g (55.1 mmol) of pinacol and molecular sieves were stirred at room temperature for 24 h. The reaction solution was filtered over celite and the solvent was removed under reduced pressure. The residue was purified chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane 0:100-50:50). 12.6 g of 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile were thus obtained. HPLC-MSa): log P=4.19, mass (m/z)=264 [(M+H)]+ 1H-NMR (400 MHz. d6-DMSO): delta=8.065 (0.8); 8.062 (0.9); 7.953 (0.5); 7.950 (0.4); 7.933 (0.6); 7.929 (0.6); 7.786 (0.9); 7.765 (0.7); 3.320 (8.9); 2.512 (3.7); 2.507 (8.0); 2.503 (11.4); 2.498 (8.7); 2.494 (4.3); 1.311 (16.0); 0.000 (0.7).
With ammonia; hydrogen In methanol at 20℃; for 16h;
2 1-[2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine
To a solution of 12.0 g (45.5 mmol) of 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile in 450 mL of 7 M methanolic ammonia solution were added 6 g of Raney cobalt and the reaction solution was stirred at room temperature under 20 bar hydrogen pressure for 16 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. 13.9 g of a pale yellow-green solid were obtained. HPLC-MSa): log P=1.27, mass (m/z)=268 [(M+H)]+
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In toluene at 110℃; for 8h; Inert atmosphere;
Step 1: Synthesis of Intermediate Bn-1
Mix 1.0 equiv of the reactant Bn, 1.2 equiv of bis(pinacolato) diboron, 0.0075 equiv of [1,1-bis(diphenylphosphino)ferrocene]palladium dichloride ( 1,1-bis(diphenylphosphino)-ferrocene dichloropalladium(II), PdCl2(dppf)), 3.0 equiv of potassium acetate (KOAc) in anhydrous toluene (0.2M), and heated at 110°C under nitrogen The mixture was stirred under ambient conditions for 8 hours, and after cooling to room temperature, distilled water was added, stirring was continued for 0.5 hours, and suction filtration was performed under vacuum. After removing the solvent from the organic layer filtrate under a low pressure environment, adding n-hexane to separate out the solid, and then filtering it under vacuum, collecting the solid and drying it and dissolving it in toluene, using toluene/n-hexane (volume ratio 5:1) as the eluent, after Purified by silica gel column chromatography to obtain a yellow-white product, which is the intermediate Bn-1.
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