Potassium Iodide → HCID 86281772, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(3,5-dimethylisoxazol-4-yl)-3-phenylindolin-2-one (1.5 g, 5 mmol), 3-bromopropan-1-ol (1.3 g, 10.0 mmol), potassium iodide (0.16 g, 1 mmol) and potassium carbonate (1.3 g, 10.0 mmol) in THF (50 mL) was heated at 60° C. for 5 hours in a capped pressure tube. The mixture was then cooled to room temperature and diluted with ethyl acetate (20 mL) and extracted with water (2×20 mL) and brine (20 mL). Aqueous layers were back washed with ethyl acetate (20 mL). Organic layers were combined, dried (MgSO4), filtered and concentrated. Residue was purified by flash chromatography (dichloromethane, then 5% ethyl acetate in dichloromethane as solvent) to give product (0.74 g, 41%). 1H NMR (400 MHz, DMSO-d6): δH 10.65 (s, 1H), 7.23-7.36 (m, 7H), 7.00 (d, J=8.0 Hz, 1H), 4.39 (m, 1H), 3.31-3.33 (m, 2H), 2.37 (s, 3H), 2.18-2.28 (m, 2H), 2.16 (s, 3H), 1.21-1.27 (m, 1H), 1.02-1.06 (m, 1H) MS (ESI) m/e [M+1]+ 363.

Provenance & Evidence