HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 475092Generated: October 30, 2026
3,4-dihydro-2H-pyran → 5-bromo-4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole
https://huagongshe.com/reaction/475092
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | 5-bromo-4-methoxy-1H-benzimidazole | HCID 178486377 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-bromo-4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole | HCID 71272697 | 60.3% |
Reaction Steps
A 500 ml tube was charged with 6-bromo-7-methoxy-1H-benzoimidazole (36 g, 0.16 mol, 1.0 equiv.), dihydropyran (40.01 g, 0.48 mol, 3.0 equiv.) and pyridinium-p-toluenesulfonate (7.96 g, 0.032 mol, 0.2 equiv.) in EtOAc (400 mL), sealed and the reaction mixture was heated at 90° C. overnight. The reaction mixture was concentrated in vacuo and the crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (30-40% EtOAc) to afford 5-bromo-4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole (30 g, 60% yield) as a brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08637537B2 |
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| Source dataset | uspto-grants-2014_01 |
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| ORD ID | ord-670a662313c846e4a66dca91aeb5c095 |
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| Source note | uspto-grants-2014_01 |
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