Sodium hydride → 4-[(2-Bromo-4-thiazolyl)methoxy]-1-(2-cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-2(1h)-pyridinone

Temperature

0 °C

To a solution of (2-bromo-1,3-thiazol-4-yl)methanol (169 mg) in DMA (5 ml) was added NaH (60% in oil, 34.9 mg) at 0° C. After being stirred at 0° C. for 30 min, 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one was added to the reaction mixture, and the mixture was stirred at 120° C. under N2 atmosphere for 30 min. The reaction mixture was quenched with water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (57.0 mg) as a white solid.

1. stirringthe mixture was stirred at 120° C. under N2 atmosphere for 30 min
2. customThe reaction mixture was quenched with water
3. extractionextracted with EtOAc
4. washThe extract was washed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. custompurified by NH silica gel column chromatography (hexane/EtOAc)

ORD record

ord-2b83714397b64e35bde56e73cdb92fb5

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2