alpha-Bromo-o-chlorotoluene → (S)-2-chloro-4-((2-chlorobenzyl)(1-methyl-5-oxopyrrolidin-3-yl)amino)benzonitrile

Participants

Reaction Steps

NaH (60% in mineral oil, 0.010 g, 0.26 mmol) was added to a solution of 2-chloro-4-{[(3S)-1-methyl-5-oxo-3-pyrrolidinyl]amino}benzonitrile (0.06 g, 0.24 mmol) in DMF (2 mL) at 0° C. under a N2 atmosphere. After stirring for 10 min, 1-(bromomethyl)-2-chlorobenzene (0.054 g, 0.26 mmol) was added and the reaction mixture was stirred at 0° C. for 15 min. The reaction was quenched with H2O and then partitioned between EtOAc and H2O. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified via column chromatography with 5% EtOAc in hexane grading to 100% EtOAc in hexane to yield the titled compound (0.03 g, 37%) as a clear oil. 1H-NMR (CDCl3) δ: 2.486 (1H, m), 2.797 (1H, m), 2.866 (3H, s), 3.383 (1H, m), 3.785 (1H, m), 4.563 (2H, m), 4.281 (1H, m), 6.519 (1H, dd, J=8.8 Hz, 2.8 Hz), 6.717 (1H, d, J=2.8 Hz), 6.757 (1H, dd, J=7.6 Hz, 1.2 Hz), 7.264 (2H, m), 7.420 (2H, m). LC-MS (ES) m/e 374.2 (M+H)+.

Provenance & Evidence