4-Chlorophenol → HCID 89783562, compound

Participants

Reaction Conditions

Reaction Steps

NaH (60% in mineral oil; 0.071 g, 1.763 mmol) was suspended in 1 mL DMF and p-chlorophenol (Aldrich; 0.174 ml, 1.763 mmol) was added. After 10 min, 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, and the reaction was sealed and heated at 70° C. for 2 h, then at 90° C. for 1 h. The reaction mixture was then treated with TFA (0.136 ml, 1.763 mmol) and 1 mL DMSO, filtered, and purified by rpHPLC (Phenomenex Gemini 150×30 mm C18 column, 20-100% ACN/H2O with 0.1% TFA); product-containing fractions were concentrated in vacuo to give 2-(2-(4-chlorophenoxy)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.044 g, 0.113 mmol, 45% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.07 (1H, br. s), 8.50 (1H, d, J=9.0 Hz), 8.11 (1H, dt, J=7.6, 0.7 Hz), 7.80 (1H, dt, J=7.9, 0.7 Hz), 7.60-7.71 (2H, m), 7.31-7.55 (4H, m), 6.94 (2H, dd, J=2.0, 0.4 Hz), 3.31-3.42 (2H, m), 2.47-2.51 (2H, m). m/z (ESI, +ve) 389.9 (M+H)+.

Provenance & Evidence