2-Fluoroaniline → 2-(2-((2-fluorophenyl)amino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Participants

Reaction Steps

To NaH (60 wt % in mineral oil; 0.071 g, 1.763 mmol) in 1 mL DMF was added 2-fluoroaniline (0.196 g, 1.763 mmol). After 10 min, a clear/colorless solution resulted. 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 as a solid and the reaction became dark red. After 30 min, the reaction was heated at 70° for 2 h. The reaction mixture was then cooled to RT and partitioned between saturated aq. NH4Cl and EtOAc. The organic layer was washed with saturated aq. NaHCO3 (1×), water (1×), saturated aq. NaCl (1×), and the organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The material was suspended in DCM and filtered, rinsing 2×DCM, dried in vacuo to give 2-(2-((2-fluorophenyl)amino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.021 g, 0.056 mmol, 22% yield) as a dull-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.04 (1H, br. s.), 9.32 (1H, s), 8.14 (1H, s), 7.97 (1H, dd, J=7.5, 1.5 Hz), 7.84-7.93 (1H, m), 7.56-7.62 (1H, m), 7.34-7.44 (1H, m), 7.22-7.33 (3H, m), 7.15-7.21 (1H, m), 6.86-6.95 (2H, m), 3.32-3.41 (2H, m), 2.51-2.57 (2H, m). m/z (ESI, +ve) 373.0 (M+H)+.

Provenance & Evidence