Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | (3-Bromophenyl)boronic acid | HCID 2734318 | — |
| Reactant | HCID 66818508 | HCID 66818508 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66818961 | HCID 66818961 | 22.5% |
Reaction Steps
{4-[3-(4-Cyano-phenoxy)-5-hydroxy-benzoylamino]-cyclohexyl}-carbamic acid isopropyl ester (1.0 g, 2.2 mmol) and copper acetate (0.4 g, 2.2 mmol), dissolved in 30 ml of dichloromethane, were charged in a 100 ml capacity seal-tube. 3-bromophenyl boronic acid (0.667 g, 3.32 mmol), 4 Å molecular sieves (3.0 g) and 0.438 g (5.53 mmol) of pyridine, in 20 ml of dichloromethane, was added to the reaction mixture in a sealed-tube and reaction mixture was stirred at RT for 20 h. After reaction completion 2.0 g of silica-gel was added and the mixture was filtered. Thus obtained filterate was concentrated under reduced pressure and subjected to column chromatography to afford 0.3 g of the required product. Percentage purity (LCMS): 86.0%, (M+1)=605.1+1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722930B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-d22e647d05674e09b8317f60370a5069 |
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| Source note | uspto-grants-2014_05 |
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