HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 82605Generated: October 30, 2026
Sodium hydride → 6-chloro-1-ethyl-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
https://huagongshe.com/reaction/82605
Participants
| Role | Name | HCID | Charge |
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| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-chloro-1-methyl-1H-1,3-benzodiazole | HCID 663080 | — |
| Reactant | 6-chloro-1-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one | HCID 58577592 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 6-chloro-1-ethyl-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one | HCID 58577290 | 79.4% |
Reaction Steps
2-Chloro-1-methyl-1H-benzimidazole (50 mg) was added to a solution of 6-chloro-1-ethyl-3-(4-hydroxyphenyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (90 mg) and NaH (13.2 mg) in DMF (2 mL) at room temperature. The mixture was heated at 180° C. for 30 min under microwave irradiation. The reaction mixture was diluted with MeOH and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0%-50% EtOAc in hexane) to give 6-chloro-1-ethyl-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (100 mg) as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08846713B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-47b698d1aaf640439f591ebf2ffaaecf |
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| Source note | uspto-grants-2014_09 |
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