Diisopropylamine → HCID 57983363, compound

Participants

Reaction Steps

2.5M n-butyllithium (6.6 mL, 16 mmol) was added to a stirred solution of diisopropylamine (2.4 mL, 17 mmol) in THF (20 mL) at −78° C. The reaction mixture was then allowed to warm to ambient temperature for 5 minutes before being cooled back down to −78° C. 2-(3-Ethynylpyridin-2-yl)-2-methylpropanenitrile (0.93 g, 5.5 mmol) was then added dropwise as a solution in THF (20 mL). After 15 minutes, ethyl chloroformate (1.7 mL, 17 mmol) in 5 mL of THF was added to the reaction. The resulting solution was allowed to warm to ambient temperature, and was then stirred for 15 minutes. TLC (30% EtOAc/hexane) showed complete reaction and a slightly lower spot than the starting material. 3 mL of MeOH was added at 8° C. and then 3 mL of H2O was added. The mixture was extracted with EtOAc, and the combined organic layers were washed with water (3×), saturated NH4Cl (3×) and brine (3×). The organic layer was then dried over MgSO4 and concentrated in vacuo. The crude product was purified by silica flash chromatography (0-75% EtOAc/hexane) to give the title compound as a white crystalline solid (0.98 g, 74%). MS (m/z)=243 (M+H)+. Calculated for C14H14N2O2 242.3.

Provenance & Evidence