Diisopropylamine → HCID 117925936, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium (1.6M in hexane, 3.65 mL, 5.85 mmol) was added dropwise over a 5-minute period to a solution of diisopropylamine (818 μL, 5.85 mmol) in 20 mL of anhydrous tetrahydrofuran held at −78° C. and under nitrogen. The reaction was warmed to 0° C., held at that temperature for 15 min, and then cooled to −78° C. The resulting solution was added dropwise over a 10 minute period to a solution of N,N-diethylpicolinamide 14 (2.09 g, 11.7 mmol) in 20 mL of anhydrous tetrahydrofuran under nitrogen at −78° C. The reaction was then allowed to warm slowly overnight to ambient temperature and then quenched with 10 mL of water and 10 mL of saturated brine. The reaction mixture was extracted with 3×30 mL of ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting oil was crystallized from ethanol/hexanes to give N,N-diethyl-3-picolinoylpicolinamide 12 (750 mg, 2.64 mmol). 1H NMR (400 MHz, DMSO-d6) δ 8.69-8.60 (m, 1H), 8.62-8.53 (m, 1H), 8.09-7.95 (m, 3H), 7.66-7.53 (m, 2H), 3.43-3.24 (m, 2H), 3.07 (q, J=7.1 Hz, 2H), 1.22 (t, J=7.0 Hz, 2H), 0.55 (t, J=7.1 Hz, 2H). LCMS: (M+H)+, 284.

Provenance & Evidence