Potassium Carbonate → HCID 178519493, compound

Temperature

85 °C

A mixture of 1-propanol (7.5 mL) and water (2.5 mL) was purged with nitrogen for 5 minutes. To the solution were added 4-bromo-1H-imidazole (146.97 mg, 1 mmol), 2-(hydroxyl-methyl)phenylboronic acid (190 mg, 1.25 mmol), Pd(OAc)2 (11.2 mg, 0.05 mmol), PPh3 (39.3 mg, 0.15 mmol) and potassium carbonate (276 mg, 2.0 mmol). After stirring at 85° C. for 16 h, the mixture was allowed to cool to room temperature and was partitioned between EtOAc (30 mL) and water (15 mL). The aqueous layer was extracted with EtOAc (2×20 mL) and the combined organic layers were washed with water, brine, and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography on silica gel to afford the pure product (62 mg, 37% yield). 1H NMR: 4.48 (s, 2H), 6.25 (br s, 1H), 7.18-7.28 (m, 2H), 7.39-7.47 (m, 2H), 7.62 (d, 1H, J=7.0 Hz), 7.80 (d, 1H), 12.30 (br s, 1H).

1. customwas purged with nitrogen for 5 minutes
2. temperatureto cool to room temperature
3. customwas partitioned between EtOAc (30 mL) and water (15 mL)
4. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
5. washthe combined organic layers were washed with water, brine
6. dry with materialdried over sodium sulfate
7. customThe solvent was removed under reduced pressure
8. customthe crude product was purified by flash column chromatography on silica gel

ORD record

ord-43313587a88a4e2f8d1082964409662a

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174942B2