N,N-Diethylaniline → HCID 57467640, compound

Temperature

210 °C

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).

1. customsealed tube
2. washthe mixture was washed over HCl (3N in water, 20 mL)
3. customThe organic layer was separated
4. customthe solvent was removed
5. dissolutionThe residue was dissolved in MeOH (10 mL)
6. additionEther (80 mL) was added
7. washthe mixture was washed with NaHCO3 (30 mL) and brine (15 mL)
8. dry with materialThe organic layer was then dried over MgSO4
9. customThe solvent was removed
10. customthe residue was purified by CombiFlash®silica gel column chromatography, eluent with hexane/EtOAc, 95/5
11. customto give T45.2 (0.30 g, 25% yield)

ORD record

ord-a96f8efc9ae341af93be3bdc8615aaa2

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748462B2