N,N,N',N'-Tetramethylethylenediamine → HCID 90087871, compound

Participants

Reaction Conditions

Reaction Steps

To a cool (−23° C.), stirred solution of N-(2,3-dichlorophenyl)pivalamide (Shimada, I. et al., Bioorganic & Medicinal Chemistry, 16:1966-1982 (2008)), compound #12; 2.10 g, 8.53 mmol) and TMEDA (1.0 ml, 6.63 mmol) in t-BuOMe (21 ml) under N2 was added n-BuLi (7.9 ml, 19.75 mmol, 2.5M in pentane) via syringe over 15 min. The reaction mixture was stirred for 90 min. To the cool reaction mixture was added a solution of N-methoxy-N-methylbenzamide (2.46 g, 14.89 mmol) in t-BuOMe (11 ml) via cannula over 30 min, then the reaction mixture was allowed to warm to room temperature as the bath warmed. To the reaction mixture was added saturated NH4Cl, then the precipitated solid was collected by filtration, washed with water, and air dried overnight to afford Intermediate A25A (2.75 g, 88%) as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.04 (1H, br. s.), 7.76-7.83 (2H, m), 7.54-7.62 (1H, m), 7.43-7.49 (2H, m), 7.41 (1H, d, J=7.7 Hz), 7.35 (1H, d, J=7.7 Hz), 1.14 (9H, s).

Provenance & Evidence