Sodium Iodide → HCID 86724072, compound

Participants

Reaction Steps

To a solution of 4-(2,4-dichloro-phenyl)-1-methyl-3-(pyridine-2-yl)-6,8-dihydro-1H-pyrazolo[3,4-e][1,4]thiazepin-7-(4H)-one (0.50 g, 1.2 mmol, prepared using C from Example 2 step B with thioglycolic acid and 2,4-dichloro-benzaldehyde) in anhydrous DMF was added cesium carbonate (0.804 g, 2.5 mmol), sodium iodide (0.370 g, 2.5 mmol) and methyl bromoacetate (0.128 mL, 1.4 mmol). The resulting mixture was stirred at rt for about 3 h, and then partitioned between ethyl acetate (50 mL) and water (25 mL). The layers were separated and the organic layer was washed with 5% aqueous sodium bicarbonate (2×25 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, DCM/ethyl acetate 9:1) to give methyl 2-(4-(2,4-dichlorophenyl)-1-methyl-7-oxo-3-(pyridin-2-yl)-6,7-dihydro-1H-pyrazolo[3,4-e][1,4]thiazepin-8(4H)-yl)acetate (0.16 g, 0.34 mmol, 28%) as a white solid: 1H-NMR (CDCl3, Bruker 400 MHz) 3.34 (1 H, d, J=17 Hz), 3.46 (1 H, dd, J=17 Hz, 2 Hz), 3.83 (3 H, s), 3.88 (3 H, s), 4.72 (1 H, d, J=15 Hz), 4.87 (1 H, d, J=15 Hz), 6.63 (1 H, d, J=9 Hz), 6.78 (1 H, d, J=2 Hz), 6.96-7.05 (2 H, m), 7.43 (1 H, d, J=2 Hz), 7.57 (1 H, dt, J=8 Hz, 2 Hz), 7.82-7.88 (1 H, m), 8.35 (1 H, m)

Provenance & Evidence