HCID 5328887, compound → HCID 44239393, compound

Temperature

50 °C

H2O2 (30% in H2O; 153 μL, 1.5 mmol) was added dropwise over 5 min to a stirred solution of 4-(2,4-dichlorophenylamino)-6,7-dimethoxyquinoline-3-carbonitrile 4c (187 mg, 0.5 mmol), concentrated H2SO4 (80 μL, 1.5 mmol), 1-Boc-3-(iodo)azetidine (282 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) in DMSO (5 mL) at 50 °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 50 °C for 45 min. Further iron(II) sulfate heptahydrate (50 mg, 0.18 mmol) was then added, followed by H2O2 (153 μL, 1.5 mmol) over 5 min. The mixture was stirred at 50 °C for 20 min. After allowing to cool, the - 20 -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 (3:2) as eluent to give the desired product 5e (118 mg, 44%). An analytical portion of the product 5e was recrystallized from EtOAc / hexanes for data purposes

ORD record

ord-6ae06cd6fdb442dfae1c1f5a96560381

Source dataset

Minisci dataset from Roche

DOI

10.1021/jo9010624