HCID 5328887, compound → HCID 44239979, compound

Temperature

60 °C

H2O2(30% in H2O; 153 μL, 1.5 mmol) was added dropwise over 5 min to a stirred solution of 4-(2,4- - 19 -dichlorophenylamino)-6,7-dimethoxyquinoline-3-carbonitrile 4c (187 mg, 0.5 mmol), concentrated H2SO4 (80 μL, 1.5 mmol), 3-iodooxetane (183 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) in DMSO (5 mL) at 60 °C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (50 mg, 0.18 mmol) was added and the mixture was stirred at 60 °C for 30 min. Further H2O2 (153 μL, 1.5 mmol) and iron(II) sulfate heptahydrate (100 mg, 0.36 mmol) was added, and the mixture was stirred at 60 °C for 15 min. After allowing to cool, the mixture was poured into a 0.1 M solution of NaOH which had been saturated with solid NaCl (50 mL) and EtOAc (50 mL). The aqueous and organic layers were partitioned and the organic layer was washed with brine (1 x 30 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography using EtOAc / hexanes (7:3) as eluent to give the desired product 5d (86 mg, 38%). An analytical portion of the product 5d was triturated with Et2O for data purposes

ORD record

ord-28ee03ebfec6486d9771f5f5dddac929

Source dataset

Minisci dataset from Roche

DOI

10.1021/jo9010624