Phenol → HCID 89783487, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of NaH (60% in mineral oil; 0.036 g, 0.898 mmol) in 0.5 mL DMF was added phenol (0.085 g, 0.898 mmol). After 10 min, 2-(2-chloroquinolin-8-yl)-7-methyl-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 27; 0.040 g, 0.128 mmol) was added and the reaction was heated to 80° C. for 2 h. The reaction was cooled, treated with DMSO and TFA (0.069 ml, 0.898 mmol), 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-methyl-2-(2-phenoxyquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.030 g, 0.081 mmol, 63% yield) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.10 (1H, br. s), 8.50 (1H, d, J=9.0 Hz), 8.13 (1H, dt, J=7.5, 0.7 Hz), 7.80 (1H, dt, J=7.9, 0.7 Hz), 7.55-7.65 (2H, m), 7.49 (1H, t, J=7.7 Hz), 7.33-7.45 (4H, m), 6.83-6.99 (2H, m), 3.44 (1H, ddt, J=12.3, 5.6, 0.6, 0.6 Hz), 2.92-3.06 (1H, m), 2.55-2.60 (1H, m), 0.90 (3H, d, J=6.8 Hz). m/z (ESI, +ve) 370.1 (M+H)+.

Provenance & Evidence