3-Fluorophenol → HCID 89783498, compound

Participants

Reaction Conditions

Reaction Steps

Prepared according to Example 103, using NaH as a 60% dispersion in mineral oil (47.0 mg, 1.176 mmol, Sigma Aldrich), 3-fluorophenol (108 μl, 1.176 mmol, Sigma Aldrich), and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 50 mg, 0.168 mmol) and heating to 85° C. for 17 h. Purification by reverse-phase HPLC (Phenomenex Gemini column, 10 micron, C18, 100 Å, 150×30 mm, 0.1% TFA in ACN/H2O, gradient 5% to 90%) to provide 2-(2-(3-fluorophenoxy)-8-quinolinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (11.2 mg, 11%) as the free base following filtration through a Si-carbonate cartridge (Silicyle) with MeOH. 1H NMR (400 MHz, MeOH-d4) δ ppm 7.10 (1H, m) 7.10 (1H, d, J=1.00 Hz) 6.80-6.87 (1H, m) 6.82 (1H, d, J=1.00 Hz) 6.44-6.49 (1H, m) 6.31-6.38 (1H, m) 6.16-6.24 (1H, m) 6.01-6.07 (1H, m) 5.87-5.99 (2H, m) 5.73 (1H, s) 2.23 (2H, t, J=1.00 Hz) 1.26 (2H, t, J=1.00 Hz). m/z (ESI, +ve) 374.1 (M+H)+.

Provenance & Evidence