3-Hydroxypyridine → HCID 89783557, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to Example 103, using NaH as a 60% dispersion in mineral oil (153 μl, 3.53 mmol, Sigma Aldrich), pyridin-3-ol (335 mg, 3.53 mmol, Sigma Aldrich), and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 150 mg, 0.504 mmol) and stirring at 25° C. for 6 h. Purification by column chromatography (silica gel, 0 to 9% MeOH/DCM) followed by trituration with MeOH provided 2-(2-(3-pyridinyloxy)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (49 mg, 27.3%). 1H NMR (400 MHz, CDCl3) δ ppm 11.07-11.15 (1H, m) 8.72-8.76 (2H, m) 8.68 (1H, d, J=1.00 Hz) 8.26 (1H, d, J=1.00 Hz) 8.04-8.09 (1H, m) 7.61-7.70 (2H, m) 7.45-7.57 (2H, m) 7.09-7.14 (1H, m) 5.38 (1H, br. s) 3.52-3.59 (2H, m) 2.54 (2H, t, J=1.00 Hz). m/z (ESI, +ve) 357.0 (M+H)+.

Provenance & Evidence