Cesium carbonate → HCID 66875433, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl-4-(3-hydroxybenzylidene)piperidine-1-carboxylate (0.500 g; Example 57, Step 3), 2-bromo5-fluoropyridine (0.456 g, 1.50 equiv), cesium carbonate (1.13 g, 2.01 equiv), and tetrakis(acetonitrile)copper(I) hexafluorophosphate (0.058 g, 0.090 equiv) in toluene (9 mL, 0.2 M) was heated to 100° C. in a Biotage Personal microwave for 10 minutes. The reaction mixture was filtered through Celite, and the Celite was washed with dichloromethane. The filtrate was concentrated and purified on 60 g silica gel using a gradient eluent consisting of 0-10% ethyl acetate/dichloromethane over 60 minutes to give the title compound as a white solid. 0.274 g, 41% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.46 (9H, s), 2.31 (2H, t, J=5.8 Hz), 2.45 (2H, t, J=5.4 Hz), 3.39 (2H, t, J=5.9 Hz), 3.49 (2H, t, J=5.9), 6.33 (1H, s), 6.85-6.98 (3H, m), 7.02 (1H, d, J=7.6 Hz), 7.33 (1H, t, J=7.8 Hz), 7.40-7.47 (1H, m), 8.03 (1H, d, J=3.1 Hz).

Provenance & Evidence