HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2209000Generated: October 31, 2026
Potassium Carbonate → 4-(benzyloxy)-6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridine
https://huagongshe.com/reaction/2209000
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 4-Benzyloxy-6-chloro-3-methyl-imidazo[4,5-c]pyridine | HCID 20820686 | — |
| Reactant | Dimethoxyphenyl boronic acid | HCID 86637092 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(benzyloxy)-6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridine | HCID 117843032 | — |
Reaction Steps
To a mixture of 4-(benzyloxy)-6-chloro-3-methyl-3H-imidazo[4,5-c]pyridine 2.25 (0.54 g, 1.97 mmol), K2CO3 (0.68 g, 4.93 mmol), Pd(dppf)Cl2 (0.07 g, 0.1 mmol), and dimethoxy phenyl boronic acid (0.65 g, 3.55 mmol) under N2 was added toluene, iPrOH, and water (2:1:1, 10 mL), and the reaction was heated to 100° C. for 5 hrs. The reaction was cooled and EtOAc (40 mL)/NaHCO3 (20 mL) were added, the layers were separated and the aqueous was extracted with EtOAc (2×25 mL). The combined organics were washed with brine (50 mL), dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (EtOAc 0-->5% MeOH gradient) to afford 4-(benzyloxy)-6-(3,4-dimethoxyphenyl)-3-methyl-3H-imidazo[4,5-c]pyridine 2.26.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09376441B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-30f13ea621c94cadaf261a85cfd8ad07 |
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| Source note | uspto-grants-2016_06 |
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