Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Chloro-3-iodobenzene | HCID 12269 | — |
| Reactant | 2,2,6,6-Tetramethyl-3,5-heptanedione | HCID 70700 | — |
| Reactant | Methyl indole-7-carboxylate | HCID 676694 | — |
| Catalyst | Cuprous chloride | HCID 62652 | — |
| Solvent | 1-Methylpyrrolidine | HCID 8454 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67147503 | HCID 67147503 | 35% |
Reaction Steps
A mixture of methyl 1H-indole-7-carboxylate (0.175 g), 3-iodo-chlorobenzene (0.358 g), Cs2CO3 (0.490 g), CuCl (0.099 g), and 2,2,6,6-tetramethyl-3,5-heptanedione (0.04 mL) in 5 mL of N-methylpyrrolidine was heated at 120° C. for 3 days. The mixture was then diluted with 50 mL of EtOAc and filtered through a pad of silica gel. The filtrate was washed with 3×15 mL of water and dried over Na2SO4. After filtration and concentration, the residue was purified by Combiflash eluted with a gradient of EtOAc/hexane to give 0.1 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07968578B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-80c96a23ca6248bea823889af2ececd6 |
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| Source note | uspto-grants-2011_06 |
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