HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(trifluoromethyl)-1,3-thiazol-4-yl)methoxy)pyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | [2-(Trifluoromethyl)-1,3-thiazol-4-yl]methanol | HCID 20079604 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 4-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one | HCID 89690863 | — |
| Solvent | Water | HCID 962 | — |
| Product | 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(trifluoromethyl)-1,3-thiazol-4-yl)methoxy)pyridin-2(1H)-one | HCID 89702264 | 22.4% |
Reaction Steps
To a mixture of 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (100 mg), (2-(trifluoromethyl)thiazol-4-yl)methanol (80 mg) and toluene (5 ml) was added potassium tert-butoxide (98 mg) at 100° C., and the mixture was stirred at the same temperature overnight. 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 (29.0 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365540B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-ef3451a9f6744524967fa48bbf7f0f20 |
| Source note | uspto-grants-2016_06 |