HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(2-formyl-3-thienyl)-1H-indole-6-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Formyl-3-thiopheneboronic acid | HCID 2773426 | — |
| Reactant | 2-Bromo-1-tert-butoxycarbonylmethyl-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester | HCID 29943315 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(2-formyl-3-thienyl)-1H-indole-6-carboxylate | HCID 86604968 | — |
Reaction Steps
Methyl 2-bromo-1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate (prepared as described in Example 1, Step 1) and (2-formyl-3-thienyl) 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 45 min; after cooling EtOAc was added and the solution washed with water and brine, dried over Na2SO4 and concentrated. The title compound was isolated by chromatography (PE/EtOAc 9:1). Yield (84%); MS (ES+) m/z 504 (M+Na)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07795247B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-f215ef09e56f4f488a04dfb2fe4ce3c5 |
| Source note | uspto-grants-2010_09 |