N,N'-Dimethylethylenediamine → HCID 89814176, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 5,5-dimethyl-4-(pyridin-3-yl)oxazolidin-2-one (0.072 g, 0.376 mmol), 4-iodo-N-(quinolin-8-yl)benzamide (0.155 g, 0.414 mmol), tribasic potassium phosphate (0.399 g, 1.880 mmol) and dioxane (3.50 mL). The mixture was purged with argon and then copper (I) iodide (0.072 g, 0.376 mmol) and N,N′-dimethylethylenediamine (0.081 mL, 0.752 mmol) were added. The system was purged with argon, the tube was sealed, and the reaction mixture was heated at 140° C. for 1 hour in a microwave. The reaction mixture was filtered through Celite® brand filter aid and the filtrate was concentrated to afford an orange brown solid. This residual material was purified by column chromatography on silica gel (RediSep 40 g column, gradient elution with 50-100% EtOAc-hexane) to afford (+/−)-(R/S)-4-(5,5-dimethyl-2-oxo-4-(pyridin-3-yl)oxazolidin-3-yl)-N-(quinolin-8-yl)benzamide (0.092 g, 0.210 mmol, 56% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.98 (s, 3H), 1.69 (s, 3H), 5.69 (s, 1H), 7.40 (dd, J=8.02, 4.79 Hz, 1H), 7.57-7.79 (m, 6H), 7.90-8.04 (m, 2H), 8.45 (dd, J=8.31, 1.66 Hz, 1H), 8.54 (dd, J=4.74, 1.61 Hz, 1H), 8.60 (br. s., 1H), 8.67 (dd, J=7.63, 1.27 Hz, 1H), 8.95 (dd, J=4.25, 1.71 Hz, 1H), 10.56 (s, 1H). m/z (ESI) 439 (M+H)+.

Provenance & Evidence