Nitrogen → HCID 86596910, compound

Participants

Reaction Steps

To a solution of diisopropylamine (1.7 mL, 12.2 mmol) in THF (50 mL) at −78° C. was added n-BuLi (6.1 mL, 2.0 M hexanes) dropwise under N2. The reaction was stirred for 30 min and 2-fluoro-N,N-diisopropyl-nicotinamide (2.75 g, 12.2 mmol) was added dropwise in a solution of THF (15 mL). The reaction was stir for 1 h, then DMF (3 mL, 36 mmol, 3 eq) was added in one portion. The reaction was stirred at −78° C. for 5 min then warmed to RT over 1 h. The reaction was quenched with NH4Cl (saturated, 100 mL), and extracted with EtOAc (2×100 mL). The combined organics were washed with brine (saturated, 200 mL), dried with Na2SO4, and purified by passing through a plug of SiO2to give pure title compound as a white solid. MS (ES+): 253.1 (M+H)+.

Provenance & Evidence