Dimethylformamide → HCID 70157614, compound

Participants

Reaction Conditions

Reaction Steps

A stirring solution of Trifluoro-methanesulfonic acid 3-[4-(5-diethylcarbamoyl-pyrimidin-2-yl)-1-(2-methyl-pentyl)-piperidin-4-yl]-phenyl ester (260 mg, 0.46 mmol), zinc cyanide (Zn(CN)2) (81 mg, 0.69 mmol) and tetrakistriphenylphosphine palladium (0) (266 mg, 0.23 mmol) in 8 mL DMF was cooled to −78° C. and de-oxygenated via a freeze-thaw process. The reaction mixture was heated to 80° C. for 1.5 hours, cooled to room temperature and filtered. The resulting solution was partitioned between EtOAc and water, the layers were separated and the aqueous layer was extracted with EtOAc (3×15 mL). The combined organic layers were dried and concentrated. The resulting crude material was purified by flash chromatography to afford 173 mg (84%) of the desired nitrile. 1HNMR (400 MHz, CDCl3) δ 8.69 (s, 2H), 7.64-7.59 (comp, 1H), 7.41-7.29 (comp, 3H), 3.51-3.49 (comp, 2H), 3.25-3.23 (comp, 2H), 2.97-2.94 (comp, 2H), 2.66 (br s, 2H), 2.27-2.25 (comp, 2H), 2.05-1.90 (comp, 4H), 1.57-1.55 (comp, 1H), 1.31-1.15 (comp, 9H), 0.99-0.95 (comp, 1H), 0.83-0.81 (comp, 6H); MS (M+1) 448.3.

Provenance & Evidence