Benzaldehyde → HCID 178519492, compound

To the stirred solution of 4-iodo-1-trityl-1H-imidazole (0.5 mmol) in THF under anhydrous condition, EtMgBr (0.33 mL, 3M in diethyl ether) was added. The reaction was allowed to stir at room temperature. After 1.5 h benzaldehyde was added and the reaction was allowed to stir overnight. After the completion of reaction few drops of methanol was carefully added at 0° C. The crude residue was used in next step without further purification. To a solution of the crude imidazole from the previous step was added acetic acid (1.0 mL) and MeOH (4.0 mL). The solution was stirred at 80° C. for 2 h. The reaction mixture was allowed to cool to room temperature and the pH was adjusted to ˜10 with 10% NaOH (aq). The aqueous phase was extracted with EtOAc (3×20 mL). The combined organic layers were washed with water, brine, and dried. The solvent was removed in vacuum to afford the crude residue, which was purified by flash column chromatography on silica gel to afford the desired product in 57% yield. 1H NMR: 1.27 (s, 1H), 5.78 (s, 1H), 6.80 (s, 1H), 7.07 (s, 1H), 7.25 (d, 1H, J=7.2 Hz), 7.32 (t, 1H, J=7.2 Hz), 7.40 (d, 1H, J=7.2 Hz), 7.64 (s, 1H), 7.74 (s, 1H)

1. stirringto stir overnight
2. additionwas carefully added at 0° C
3. customThe crude residue was used in next step without further purification
4. additionTo a solution of the crude imidazole from the previous step was added acetic acid (1.0 mL) and MeOH (4.0 mL)
5. stirringThe solution was stirred at 80° C. for 2 h
6. temperatureto cool to room temperature
7. extractionThe aqueous phase was extracted with EtOAc (3×20 mL)
8. washThe combined organic layers were washed with water, brine
9. customdried
10. customThe solvent was removed in vacuum
11. customto afford the crude residue, which
12. customwas purified by flash column chromatography on silica gel

ORD record

ord-52a39bb617174ee0a5f5614c13ecb35e

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722720B2