Phenol → HCID 89784005, compound

Participants

Reaction Conditions

Reaction Steps

To NaH (60 wt % in mineral oil; 0.047 g, 1.176 mmol) in 1 mL DMF was added phenol (0.111 g, 1.176 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, 0.050 g, 0.168 mmol) was added and the reaction became dark red. After 30 min at RT, the reaction was heated to 70° C. The reaction was judged complete after 5 h at 70° C., and was cooled to RT and quenched with saturated aq. NH4Cl and EtOAc. The organic layer was sequentially washed with water, and saturated aq. NaCl, then dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The material was treated with DCM and purified by silica gel chromatography using 0-50%-90/10 DCM/MeOH in DCM. The product-containing fractions were concentrated to afford 2-(2-phenoxyquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.048 g, 0.135 mmol, 80% yield) as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.04 (1H, br. s), 8.49 (1H, d, J=8.8 Hz), 8.12 (1H, dd, J=7.6, 1.6 Hz), 7.74-7.87 (1H, m), 7.56-7.66 (2H, m), 7.33-7.52 (5H, m), 6.84-7.01 (2H, m), 3.31-3.38 (2H, m), 2.39 (2H, t, J=6.9 Hz). m/z (ESI, +ve) 356.0 (M+H)+.

Provenance & Evidence