Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl Acrylate | HCID 7294 | — |
| Reactant | 6-Bromoindole | HCID 676493 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 54059723 | HCID 54059723 | 73% |
Reaction Steps
To a resealable reaction tube was added 6-bromoindole (5 g, 26 mmol), methyl acrylate (2.9 ml, 32 mmol), TEA (4.4 ml, 32 mmol), (o-Tol)3P (0.78 g, 2.6 mmol) and Pd(OAc)2 (0.29 g, 1.3 mmol). The reaction tube was sealed and the resulting mixture was stirred at 100° C. for 20 hours, then cooled to room temperature, diluted with DCM, and filtered through celite. The filter cake was washed with DCM. The filtrate was concentrated and purified via flash chromatography (hexane/EtOAc) to provide 3-(1H-indol-6-yl)-acrylic acid methyl ester XXX (3.8 g, 73% yield) as a bright yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07803830B2 |
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| Source dataset | uspto-grants-2010_09 |
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| ORD ID | ord-0eb544c59e8f45928fa3b7bff83daace |
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| Source note | uspto-grants-2010_09 |
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