HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → {4-[3-(1-Cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-yloxymethyl]-phenoxy}-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Acetic acid, 2-[4-(bromomethyl)phenoxy]-, methyl ester | HCID 67049717 | — |
| Reactant | 3-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-ol | HCID 178517706 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | {4-[3-(1-Cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-yloxymethyl]-phenoxy}-acetic acid methyl ester | HCID 67049940 | 50% |
Reaction Steps
To a stirred solution of 3-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-ol (58 mg, 0.17 mmol) in acetone (10 ml) was added cesium carbonate (0.085 g, 0.26 mmol) followed by (4-bromomethyl-phenoxy)-acetic acid methyl ester (49 mg, 0.19 mmol; CAS Reg. No. 104508-23-8) and the reaction mixture was refluxed for 2 h. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography using silica gel (50-60% ethyl acetate/n-hexane) to yield the desired compound as a brown solid (50%). MS (Turbo Spray): m/z=522.5 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309581B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-9ec85166ca7e4c7cbfc6b5d27383b1da |
| Source note | uspto-grants-2012_11 |