N,N-Diethylaniline → HCID 57467640, compound

Participants

Reaction Conditions

Reaction Steps

The reaction mixture of T45.1 (1.2 g, 5.0 mmol), N,N-diethylaniline (3.0 mL, 16 mmol) and N,O-bis(trimethylsilyl)acetamide (2.0 mL, 8 mmol) in a 15 mL sealed tube was heated at 210° C. for 48 hours. Ether (60 mL) was added, and the mixture was washed over HCl (3N in water, 20 mL). The organic layer was separated, and the solvent was removed. The residue was dissolved in MeOH (10 mL) and HCl (3N in water, 2 mL) and was stirred at room temperature for 30 minutes. Ether (80 mL) was added, and the mixture was washed with NaHCO3 (30 mL) and brine (15 mL). The organic layer was then dried over MgSO4. The solvent was removed, and the residue was purified by CombiFlash®silica gel column chromatography, eluent with hexane/EtOAc, 95/5 to give T45.2 (0.30 g, 25% yield). MS ESI (pos.) m/e: 221.2 (M+H)+. 1H NMR (500 MHz, CDCl3) δ ppm 8.01 (1H, d, J=2.0 Hz), 7.87 (1H, dd, J=8.4, 2.0 Hz), 6.87 (1H, d, J=8.4 Hz), 6.32 (1H, s), 6.21 (1H, dd, J=17.9, 10.5 Hz), 5.24-5.45 (2H, m), 3.90 (3H, s), 1.48 (6H, s).

Provenance & Evidence