Ammonium Chloride → N-(3-tert-butylphenyl)-2-(2,2-dimethylpropyl)nicotinamide

2,2-Dimethylpropylmagnesium chloride (1 M-diethylether, 4.8 mL, 4.8 mmol) was added to a suspension of copper cyanide (215 mg, 2.40 mmol) in THF (6 mL) at −78° C. After stirring at the same temperature for 1 hour, 2-bromo-N-(3-tert-butylphenyl)nicotinamide (200 mg, 0.601 mmol) was added all at once as a solid. The reaction mixture was gradually warmed to room temperature and the reaction was allowed to stir overnight. Saturated ammonium chloride solution and ethyl acetate was added, and the reaction mixture was filtered through celite and rinsed with ethyl acetate. The layers were separated and the product was extracted once more with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the crude material was purified using silica gel column chromatography using a gradient of 20%-50% ethyl acetate in hexanes to yield N-(3-tert-butylphenyl)-2-(2,2-dimethylpropyl)nicotinamide (168 mg, 0.517 mmol, 86%). Rf=0.45 (toluene: ethyl acetate=2:1).

1. stirringto stir overnight
2. filtrationthe reaction mixture was filtered through celite
3. washrinsed with ethyl acetate
4. customThe layers were separated
5. extractionthe product was extracted once more with ethyl acetate
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. customAfter removing the solvent under reduced pressure
9. customthe crude material was purified

ORD record

ord-011b8290da3343feaad711cbce68a933

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126939B2