Ethyl bromoacetate → Ethyl [7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetate

Participants

Reaction Steps

7-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (Example 17) (100 mg, 0.238 mmol), ethyl bromoacetate (0.043 ml, 0.391 mmol) and cesium carbonate (170 mg, 0.521 mmol) were stirred at room temperature in DMF for 5 hours. The reaction mixture was diluted with diethyl ether (˜20 ml) and washed with water (2ט20 ml), the organic layer was passed through a phase separating cartridge to dry and concentrated in vacuo to yield the title compound (77 mg, 0.16 mmol, 60% yield) as a yellow oil. δH (d6DMSO, 400 MHz): 8.19 (1H, s), 8.11 (1H, dd), 7.81-7.85 (2H, m), 7.45 (1H, d), 7.34 (1H, d), 4.89 (1H, sept), 4.07 (2H, q) 3.42 (2H, s), 3.00-291 (4H, m), 2.77-2.72 (4H, m), 1.36 (6H, d), 1.19 (3H, t). MS (ES): C25H2835ClN3O4 requires 469; found 470 [M+H]+.

Provenance & Evidence