反应详情

A solution of 2-[(1-methylethyl)oxy]-5-[3-(1,2,3,4-tetrahydro-5-isoquinolinyl)-1,2,4-oxadiazol-5-yl]benzonitrile (Preparation 7, 50 mg, 0.139 mmol) and N-bromosuccinimide (29.6 mg, 0.166 mmol) in DCM (5 mL) was heated at reflux for 3 h, then cooled to room temperature. 2M aqueous NaOH (5 mL) was added, and the layers separated. The aqueous was extracted with DCM (5 mL) and the organic layers combined. Concentration in vacuo gave the title compound as a yellow solid (47.8 mg). 1H NMR (400 MHz, CDCl3) δ 8.52 (1H, t), 8.43 (1H, d), 8.34 (1H, dd), 8.23 (1H, dd), 7.55-7.51 (2H, m), 7.14 (1H, d), 4.81 (1H, sept), 3.86 (2H, td), 3.31 (2H, t), 1.48 (6H, d); m/z (ES) 359 [M+H]+.

1. temperatureat reflux for 3 h
2. customthe layers separated
3. extractionThe aqueous was extracted with DCM (5 mL)
4. concentrationConcentration in vacuo