Pyridine → HCID 68242808, compound

Molecular sieve 4A (4.88 g), copper (II) sulfate (7.71 g), phenylboronic acid (6.76 g), and pyridine (4.49 mL) were added to a solution of 4-cyanomethylimidazole (3.00 g) in methylene chloride (120 mL), and the mixture was stirred overnight at room temperature under an air atmosphere at normal pressure. The reaction solution was filtered through celite and washed with methylene chloride. Then, a saturated aqueous solution of sodium bicarbonate (200 mL) and disodium dihydrogen ethylenediaminetetraacetate dihydrate (15.5 g) were added to the filtrate, and the mixture was stirred at room temperature for 20 minutes. After separation into aqueous and organic layers, the organic layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the obtained crude product was purified by silica gel column chromatography to obtain the title compound (2.34 g).

1. filtrationThe reaction solution was filtered through celite
2. washwashed with methylene chloride
3. additionThen, a saturated aqueous solution of sodium bicarbonate (200 mL) and disodium dihydrogen ethylenediaminetetraacetate dihydrate (15.5 g) were added to the filtrate
4. stirringthe mixture was stirred at room temperature for 20 minutes
5. customAfter separation into aqueous and organic layers
6. washthe organic layer was washed with saturated sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationAfter filtration and concentration under reduced pressure
9. customthe obtained crude product
10. customwas purified by silica gel column chromatography

ORD record

ord-0ca8d2b7346e4f279cbd0aa6032cebf5

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946443B2