Reacción #1904056

Ecuación de reacción

Ethyl acetate

5-[5-methyl-2-oxo-5-(2-thienyl)-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl]-1H-pyrrole-2-carbonitrile

potassium carbonate

iodomethane

→

title compound

Rendimiento 22.0%

1-Methyl-5-[5-methyl-2-oxo-5-(2-thienyl)-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl]-1H-pyrrole-2-carbonitrile

Rendimiento 22.0%

Disolventes

brine

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroorganic layer separated
2. 2
   Secadodried (Mg2SO4)
3. 3
   Concentraciónconcentrated
4. 4
   OtroThe residue was purified by a flash chromatography on a silica gel column (hexane:ethyl acetate/2:1)

Procedimiento

To a solution of 5-[5-methyl-2-oxo-5-(2-thienyl)-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl]-1H-pyrrole-2-carbonitrile (0.1 g, 0.29 mmol) in anhydrous DMF (5 mL) at rt under nitrogen was added potassium carbonate (1 g, 7.23 mmol) and iodomethane (0.5 mL, 8 mmol). The reaction mixture was stirred for 2 h and treated with brine (30 mL). Ethyl acetate (50 mL) was added and organic layer separated, dried (Mg2SO4), and concentrated. The residue was purified by a flash chromatography on a silica gel column (hexane:ethyl acetate/2:1) to afford the title compound as a white solid (23 mg, 22%): mp 197-198° C.; 1H-NMR (DMSO-d6) δ 10.21 (s, 1H), 7.55 (d, J=4.8, 1H), 7.43 (dd, J=8.4, 1.8 Hz, 1H), 7.35 (d, J=1.8 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 7.01 (d, J=4.1 Hz, 1H), 6.98 (d, J=4.9 Hz, 1H), 6.93 (d, J=3.0 Hz, 1H), 6.31 (d, J=4.1 Hz, 1H), 4.21 (d, J=15.9 Hz, 1H), 4.07 (d, J=15.9 Hz, 1H), 3.65 (s, 3H), 2.04 (s, 3H). MS (ES) m/z 362 ([M−H]−, 100%).

Fuente