N-Ethylaniline → HCID 89783659, compound

Participants

Reaction Steps

NaHMDS (1.0 M solution in THF; 1.975 ml, 1.975 mmol) was added to N-ethylaniline (0.249 ml, 1.975 mmol) and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 0.084 g, 0.282 mmol). The dark red reaction was stirred rapidly at RT. After 2 h, the reaction was quenched with saturated aq. NH4Cl. The reaction 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. This material was dissolved in DMSO and purified by rpHPLC (Phenomenex Gemini 150×30 mm C18 column, 10-80% ACN/H2O with 0.1% TFA); product-containing fractions were treated with saturated aq. NaHCO3 and DCM. The combined organic layers were then the aq. layer was extracted 3×DCM, the combined organics layers were then dried over Na2SO4, filtered, and concentrated in vacuo to give 2-(2-(ethyl(phenyl)amino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.044 g, 0.115 mmol, 40.8% yield) as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.07-12.29 (1H, m), 7.92-8.19 (2H, m), 7.48-7.63 (3H, m), 7.34-7.47 (3H, m), 7.26 (1H, t, J=7.6 Hz), 6.98-7.07 (1H, m), 6.89-6.98 (1H, m), 6.83 (1H, d, J=9.2 Hz), 4.08 (2H, q, J=7.0 Hz), 3.36-3.44 (2H, m), 2.69 (2H, t, J=6.9 Hz), 1.30 (3H, t, J=7.0 Hz). m/z (ESI, +ve) 383.0 (M+H)+.

Provenance & Evidence