Carbon tetrabromide → HCID 68528577, compound

Temperature

0 °C

A solution of (4-{5-[4-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-furyl)methanol (0.20 g, 0.50 mmol) that was obtained in Example 1 (1e), carbon tetrabromide (0.20 g, 0.60 mmol), and triphenylphosphine (0.16 g, 0.60 mmol) in dichloromethane (1.0 ml) was stirred at 0° C. for 1 hour. Subsequently, to the reaction mixture were added successively ethyl 3-azetidinecarboxylate hydrochloride (0.12 g, 0.75 mmol) and N,N-diisopropylethylamine (0.26 ml, 1.5 mmol) at the same temperature with stirring, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, a saturated aqueous solution of sodium hydrogencarbonate (1.0 ml) was added to the reaction mixture to quench the reaction, and the resulting mixture was poured into water (20 ml) and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1 to 2:1) as the eluent to afford the title compound (0.21 g) in a yield of 84% as a white crystalline solid.

1. stirringwith stirring
2. stirringthe resulting mixture was stirred at room temperature for 2 hours
3. stirringAfter stirring
4. customto quench
5. customthe reaction
6. extractionextracted with ethyl acetate
7. washThe extract was washed with a saturated aqueous solution of sodium chloride
8. dry with materialdried over magnesium sulfate
9. filtrationAfter filtration
10. customthe filtrate was evaporated in vacuo

ORD record

ord-5a815ec873a34b5fb1c09b3a7ae62f26

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2