Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 11341533 | HCID 11341533 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene water | HCID 22272177 | — |
| Product | HCID 11477141 | HCID 11477141 | 29.5% |
Reaction Steps
A mixture of 150 mg (0.283 mmol) 4-bromo-5-iodo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole (example 30), 38 mg (0.312 mmol) phenylboronic acid, 60 mg (0.567 mmol) sodium carbonate and 16 mg (0.014 mmol) tetrakis(triphenylphosphine)palladium in 6 ml toluene/water (3:1) is stirred at 100° C. for 12 h. Then the reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 40 mg of the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08030497B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-4264ad9b305e4d21929a5b2b91075309 |
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| Source note | uspto-grants-2011_10 |
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