Ammonia → HCID 68524051, compound

To a solution of [(4-bromo-2-thienyl)methoxy]t-butyldimethylsilane (9.0 g, 29 mmol) [reference literature: J. Med. Chem., vol. 45, 5005 (2002)] in N,N-dimethylformamide (20 ml) was added copper cyanide (4.7 g, 53 mmol) with stirring, and the resulting mixture was refluxed for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ether (80 ml), and after adding a 28% aqueous solution of ammonia (50 ml), the resulting mixture was stirred at room temperature for 1 hour. After stirring, the reaction mixture was extracted with ether, and the extract was washed successively with water and a saturated aqueous solution of sodium chloride and dried over sodium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:50 to 1:4) as the eluent to afford the title compound (4.3 g) in a yield of 58% as a colourless oily product.

1. temperaturethe resulting mixture was refluxed for 2 hours
2. stirringthe resulting mixture was stirred at room temperature for 1 hour
3. stirringAfter stirring
4. extractionthe reaction mixture was extracted with ether
5. washthe extract was washed successively with water
6. dry with materiala saturated aqueous solution of sodium chloride and dried over sodium sulfate
7. filtrationAfter filtration
8. customthe filtrate was evaporated in vacuo

ORD record

ord-5c905a7b41f64b659d914a89f7e3c4fa

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2