1,2-Dichloroethane → HCID 57575221, compound

Participants

Reaction Steps

To a solution of 4-((3-fluorophenyl)ethynyl)benzoic acid (2.0 g, 8.33 mmol) and DIPEA (2.38 g, 18.3 mmol) in DMF (35 mL) was added EDC (1.86 g, 10.0 mmol), HOBt (1.35 g, 10.0 mmol) and morpholine (1.07 g, 12.5 mmol). The reaction was stirred at room temperature for 18 h. The reaction was diluted with water (200 mL) and extracted with EtOAc (2×150 mL). The combined organic extracts were washed with water (2×100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by column chromatography (silica gel) using 0 to 90% EtOAc/hexanes to afford (4-((3-fluorophenyl)ethynyl)phenyl)(morpholino)methanone (2.35 g, 89%) as a light tan solid; 1H-nmr (400 MHz, CDCl3) δ 7.57 (d, J=8.5 Hz, 2H), 7.41 (d, J=8.5 Hz, 2H), 7.38-7.31 (m, 2H), 7.28-7.21 (m, 1H), 7.13-7.05 (m, 1H), 4.00-3.31 (bd s, 8H); LC (290 nM) 5.08 min (>98%); MS (ESI) m/z=310.

Provenance & Evidence