HuagongsheHuagongshe Chemistry Print Report · For research reference only
3,4-dihydro-2H-pyran → 5-bromo-4-chloro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- | HCID 18462 | — |
| Reactant | 5-bromo-4-chloro-1H-benzoimidazole | HCID 59474483 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-bromo-4-chloro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole | HCID 71272154 | 90.1% |
Reaction Steps
To a solution of 128 (22 g, 0.095 mol) in dry THF (660 mL) was added 3,4-dihydro-2H-pyran (24 g, 0.286 mol) and camphorsulfonic acid (2.2 g, 0.00948 mol) and the solution was heated to reflux for 16 h. The resulting mixture was concentrated, and the residue obtained was purified by SiO2 chromatography eluting with 20% EtOAc/petroleum ether to afford 27 g (90%) of 5-bromo-4-chloro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole (130) as pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637537B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-be6b7e4c6dae4163833849915c796a05 |
| Source note | uspto-grants-2014_01 |