Selenium Dioxide → HCID 11854408, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-methyl-N-(2-methylbenzo[d]thiazol-5-yl)-4-(3,3-dimethylbut-1-ynyl)benzamide (50 mg, 0.14 mmol), selenium dioxide (46 mg, 0.41 mmol), and 1,4-dioxane (10 mL) was stirred under an atmosphere of nitrogen at 80° C. overnight. After cooling, the mixture was filtered through Celite® and the filtrate was treated with aq. NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated under vacuum. The residue was dissolved in THF-H2O (2:1) (10 mL) and NaBH4 (50 mg) was added slowly. The mixture was stirred at rt for 2 h and then acidified with 1N HCl. After treated with aq. NaHCO3, the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated under vacuum. The residue was purified by preparative thin-layer chromatography to give N-(benzo[d]thiazol-5-yl)-2-methyl-4-(3,3-dimethylbut-1-ynyl)benzamide (compound 198-11 mg) as a light yellow solid and N-(2-(hydroxymethyl)benzo[d]thiazol-5-yl)-2-methyl-4-(3,3-dimethylbut-1-ynyl)benzamide (compound 197-27 mg) as a light yellow solid.

Provenance & Evidence