4-Chloroaniline → HCID 89784513, compound

Participants

Reaction Steps

To 4-chloroaniline (Alfa Aesar, Ward Hill, Mass.; 0.225 g, 1.763 mmol) and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 0.075 g, 0.252 mmol) was added LHMDS (1.0 M solution in THF; 1.763 ml, 1.763 mmol). After 3 h, the reaction mixture was partitioned between saturated aq. NH4Cl and DCM. The aq. layer was extracted with DCM (3×), and the combined organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. EtOAc was added, the layers were separated, and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The solid was suspended in MeOH and filtered, rinsing 1× MeOH to give 2-(2-((4-chlorophenyl)amino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.017 g, 0.044 mmol, 17% yield) as a dull-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.96 (1H, br. s), 9.62 (1H, s), 8.12 (1H, d, J=9.0 Hz), 7.89 (1H, dt, J=7.2, 0.8 Hz), 7.72-7.81 (2H, m), 7.61 (1H, dt, J=7.8, 0.9 Hz), 7.36-7.46 (2H, m), 7.31 (1H, t, J=7.6 Hz), 7.08 (1H, d, J=9.0 Hz), 6.88-7.00 (2H, m), 3.37-3.52 (2H, m), 2.70 (2H, t, J=6.9 Hz). m/z (ESI, +ve) 389.0 (M+H)+.

Provenance & Evidence