Dimethyl Sulfoxide → HCID 71295558, compound

Temperature

-78 °C

To a solution of Oxalyl dichloride (10 ml) in dichloromethane (10 mL), was treated with DMSO (2 mL) in dichloromethane (10 mL) by dropwise at −78° C., the solution was stirred at −78° C. for another 10 min, then trans-2-(5-bromo-2-methoxypyridin-3-yl)-3a,4,5,6,7,7a-hexahydro-1H-benzo[d]imidazole (1 g, 3.3 mmol) was added in one portion under N2 protection. The react solution was stirred at −60° C. for 30 min, triethylamine is added over 5 min and the mixture was stirred at R.T. overnight. The resulting solution was treated with ice-cold 1 M hydrochloric acid solution (10 mL), the two phases are separated, the aqueous phase was extracted with dichloromethane (2*30 mL), and the combined organic phases was washed with pH 7 aqueous phosphate buffer (2*20 mL), then dried with anhydrous sodium sulfate and concentrated under reduced pressure to provide 2-(5-bromo-2-methoxypyridin-3-yl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole (0.78 g, yield 78.8%) as a solid. 1HNMR (400 MHz, DMSO) δ 14.5 (br, 1H), 8.78 (d, J=2 Hz, 1H), 8.50 (d, J=2 Hz, 1H), 4.04 (s, 3H), 3.15 (s, 4H), 2.66 (s, 4H). MS (M+H)+: 310/312. MS (M+H)+: 308/310.

1. stirringThe react solution was stirred at −60° C. for 30 min
2. stirringthe mixture was stirred at R.T. overnight
3. customthe two phases are separated
4. extractionthe aqueous phase was extracted with dichloromethane (2*30 mL)
5. washthe combined organic phases was washed with pH 7 aqueous phosphate buffer (2*20 mL)
6. dry with materialdried with anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-4e0bbd5e895a4acdb20a508ed796f0ad

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09265773B2