Phenol → HCID 89784031, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of NaH (60% in mineral oil; 0.064 g, 1.611 mmol) in 1 mL DMF was added phenol (0.152 g, 1.611 mmol). After 10 min, rac-2-(2-chloroquinolin-8-yl)-7-ethyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 22; 0.075 g, 0.230 mmol) was added, and the reaction was heated to 70° C. After 2 h, the reaction was cooled and treated with TFA (0.124 ml, 1.611 mmol) and 1 mL DMSO, and the solution was filtered and purified by rpHPLC (Phenomenex Gemini 150×30 mm C18 column, 15-100% ACN/H2O with 0.1% TFA); product-containing fraction was treated with saturated aq. NaHCO3 and DCM. The organic layer was separated, and the aq. layer was extracted 3×DCM. The combined organic layers were then dried over Na2SO4, filtered, and concentrated in vacuo to give rac-7-ethyl-2-(2-phenoxyquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.035 g, 0.091 mmol, 40% yield) as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.12 (1H, br. s), 8.50 (1H, d, J=8.8 Hz), 8.14 (1H, dt, J=7.5, 0.7 Hz), 7.80 (1H, dt, J=8.0, 0.7 Hz), 7.35-7.64 (7H, m), 6.90-7.00 (1H, m), 6.82-6.91 (1H, m), 3.38-3.45 (1H, m), 3.12-3.20 (1H, m), 2.24-2.34 (1H, m), 1.13-1.34 (2H, m), 0.82 (3H, t, J=7.3 Hz). m/z (ESI, +ve) 384.0 (M+H)+.

Provenance & Evidence