Methanol → 5-(4-Iodophenyl)-3-methyl-1,2,4-oxadiazole

1,1′-Carbonyldiimidazole (0.49 g, 3 mmol) was added to a solution of 4-iodobenzoic acid (0.5 g, 2 mmol) in dry dimethylformamide (4 ml) and stirred at room temperature for 30 minutes. N-hydroxy-acetamidine (0.224 g, 3 mmol) was added and stirring at room temperature continued for 16 hours. Sodium methoxide in methanol (25% wt solution; 1.1 ml, 5 mmol) was added and the mixture heated at 80° C. for 6 hours. Once cool, ethyl acetate (50 ml) and water (50 ml) were added. The organic layer was washed with water (50 ml), brine (50 ml), dried over magnesium sulfate, filtered and solvent removed in vacuo. The residue was purified by silica SPE cartridge (5 g) (100% cyclohexane, 20:1 cyclohexane/ethyl acetate v:v to 10:1 cyclohexane/ethyl acetate v:v) to yield the desired product as a white solid (0.15 g, 0.52 mmol).

1. stirringstirring at room temperature
2. waitcontinued for 16 hours
3. temperaturethe mixture heated at 80° C. for 6 hours
4. temperatureOnce cool
5. washThe organic layer was washed with water (50 ml), brine (50 ml)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. customsolvent removed in vacuo
9. customThe residue was purified by silica SPE cartridge (5 g) (100% cyclohexane, 20:1 cyclohexane/ethyl acetate v:v to 10:1 cyclohexane/ethyl acetate v:v)

ORD record

ord-2dc827775f15424f9227b48bef98f4d9

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07425555B2