Dimethylformamide → HCID 54675676, compound

Participants

Reaction Steps

A DMF (5 mL) solution of the crude intermediate from Step C (ca 0.24 mmol), copper (I) iodide (45.3 mg, 0.24 mmol) and N,N′-dimethylethylenediamine (25.2 mg, 0.29 mmol) was stirred at ambient temperature for 1 hour. The reaction mixture was diluted with EtOAc and washed with 10% aqueous NH4OH solution (2×), water (2×), 0.5 N HCl (1×), and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by preparative thin layer chromatography using 5% MeOH/CHCl3 as eluent. The isolated material was purified again by silica gel column chromatography using a hexanes/EtOAc gradient to give the indicated compound. 1H NMR (500 MHz, DMSO-d6): δ (ppm) 11.19 (1H, s), 8.86 (1H, d, J=9.0 Hz), 7.93 (1H, d, J=2.0 Hz), 7.55-7.43 (2H, m), 7.34-7.24 (5H, m), 7.20 (1H, t, J=9.7 Hz), 6.74 (2H, s), 4.46 (2H, s), 1.77 (3H, s). m/z=535.4 (M+H).

Provenance & Evidence