Sodium Carbonate → 4-[2-(3-Benzyl-[1,2,4]oxadiazol-5-yl)-vinyl]benzene-1,2-diol

Temperature

-78 °C

3-Benzyl-5-[2-(3,4-dimethoxy-phenyl)-vinyl-]-[1,2,4]oxadiazole (compound of Example 4, Method A, Step 1; 0.180 g, 0.55 mmol) was dissolved in dichloromethane (7 mL) and cooled to −78° C. A solution of boron tribromide (0.41 mL, 4.40 mmol) in dichloromethane (4 mL), which was cooled to 0° C., was added slowly over a period of 15 min. After 3 h, the reaction mixture was warmed to room temperature and stirred for 3 h. After completion of the reaction, the mixture was quenched by dropwise addition of methanol (15 mL) at 0° C. and stirred for 20 min at room temperature. The solvent was evaporated and the residue obtained was redissolved in 10% methanol in chloroform at 0° C., followed by stirring with solid sodium carbonate to maintain pH ˜8. The solvent was evaporated and the crude product obtained was purified by column chromatography (silica gel, 0.5% methanol in chloroform) to afford the title compound.

1. additionwas added slowly over a period of 15 min
2. temperaturethe reaction mixture was warmed to room temperature
3. customAfter completion of the reaction
4. customthe mixture was quenched by dropwise addition of methanol (15 mL) at 0° C.
5. stirringstirred for 20 min at room temperature
6. customThe solvent was evaporated
7. customthe residue obtained
8. temperatureto maintain pH ˜8
9. customThe solvent was evaporated
10. customthe crude product obtained
11. customwas purified by column chromatography (silica gel, 0.5% methanol in chloroform)

ORD record

ord-415a127de0104a09b58344a76848b248

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629277B2