2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 89783941, compound

Participants

Reaction Steps

To a solution of 2-(2-phenoxyquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 37; 0.07 g, 0.197 mmol) in 1,4-dioxane (20 mL) was added DDQ (0.134 g, 0.591 mmol), and the reaction was stirred at RT for 2.5 h. The mixture was diluted with ice water (50 mL) and extracted with EtOAc (50 mL). The organic layer was separated, dried, filtered and concentrated. The residue was purified with preparative HPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 30-90% ACN in water with 0.1% TFA) to give 2-(2-phenoxyquinolin-8-yl)-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.034 g, 49%) as a pale brown solid. MS (ESI, pos. ion) m/z: 354.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.28 (s, 1H), 10.73 (d, 1H, J=5.2 Hz), 8.54 (d, 1H, J=8.9 Hz), 8.31 (d, 1H, J=7.1 Hz), 7.89 (d, 1H, J=7.6 Hz), 7.67 (t, J=7.8 Hz, 2H), 7.54 (t, J=7.6 Hz, 2H), 7.44-7.47 (m, 3H), 7.24 (d, 1H, J=1.3 Hz), 6.90-7.03 (m, 1H), 5.87 (d, 1H, J=7.0 Hz).

Provenance & Evidence