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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2203110Generated: November 2, 2026

Sodium hydride → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(difluoromethyl)-1,3-thiazol-2-yl)methoxy)pyridin-2(1H)-one

https://huagongshe.com/reaction/2203110

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
ReactantDimethylacetamideHCID 31374—
Reactant2-Thiazolemethanol, 4-(difluoromethyl)-HCID 68096379—
Reactant4-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-oneHCID 89690863—
SolventWaterHCID 962—
Product1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(difluoromethyl)-1,3-thiazol-2-yl)methoxy)pyridin-2(1H)-oneHCID 8969100719.7%

Reaction Conditions

Temperature120 °C

Reaction Steps

A mixture of (4-(difluoromethyl)-1,3-thiazol-2-yl)methanol (50 mg), 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-2(1H)-one (69.5 mg), NaH (60% in oil, 12.1 mg) and DMA (1 ml) was heated at 120° C. under microwave irradiation for 2 h. The mixture was poured into water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (17 mg) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365540B2
Source datasetuspto-grants-2016_06
ORD IDord-0ea125f01e2b47f7ac6140b61cc78057
Source noteuspto-grants-2016_06