HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → methyl 3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Vinylbenzeneboronic acid | HCID 2773587 | — |
| Reactant | Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate | HCID 11175076 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | methyl 3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate | HCID 58765232 | 91% |
Reaction Steps
Methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (prepared as described in WO 2004065367) and (2-vinylphenyl)boronic acid (1.5 eq) were dissolved in dioxane (0.07 M) and 2M aqueous Na2CO3 (6 eq) was added. The solution was degassed by bubbling argon, Pd(PPh3)2Cl2 (0.2 eq) was added, and the reaction mixture was refluxed for 1 h; after cooling, EtOAc was added, and the solution washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The title compound was isolated by chromatography (PE/EtOAc 9:1) in 91% yield; MS (ES+) m/z 360 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07795247B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-992665e823c74d15a69e3aef5585f2eb |
| Source note | uspto-grants-2010_09 |