2-Methylquinoxaline → HCID 44239813, compound

Temperature

60 °C

H2O2 (35% in H2O; 0.53 mL, 6.0 mmol) was added to a stirred solution of 2-methylquinoxaline 1h (288 mg, 2.0 mmol), concentrated H2SO4 (107 μL, 1.0 mmol), 3-iodooxetane (368 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (167 mg, 0.6 mmol) in DMSO (17 mL) at 60 °C. The mixture was stirred at 60 °C for 30 min then further H2O2 (0.53 mL, 6.0 mmol) and iron(II) sulfate heptahydrate (167 mg, 0.6 mmol) was added, and the mixture was stirred at 60 °C for 30 min. One last portion of H2O2 (0.53 mL, 6.0 mmol) and iron(II) sulfate heptahydrate (167 mg, 0.6 mmol) was added, and the mixture was stirred at 60 °C for 30 min. After allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (50 mL) and extracted with EtOAc (3 x 30 mL). The combined organic extracts were washed with brine (3 x 50 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gels using MeOH / CH2Cl2 (0:1 to 1:19) as eluent, followed by purification by preparative high-performance liquid chromatography to give the desired product 2h (94 mg, 22%) as a solid

ORD record

ord-692777e0346141d795b86ad587ec5cde

Source dataset

Minisci dataset from Roche

DOI

10.1021/jo9010624