Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Butenoic acid, 4-bromo-, methyl ester | HCID 5369175 | — |
| Reactant | 1-(6-Bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)ethan-1-one | HCID 21948380 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21833029 | HCID 21833029 | 68% |
Reaction Steps
1-Acetyl-6-bromo-5-hydroxyindoline (Tetrahedron, 1973, 29 (8), 1115) (2.54 g, 10 mmol) was stirred under Ar in dry DMF (50 ml) as sodium hydride (80%, 0.33 g, 11 mmol) was added over 10 min. After a further 10 min, methyl 4-bromocrotonate (1.75 ml, 15 mmol) was added. The mixture was stirred at 60° C. for 2 h, cooled, and diluted with water. The precipitated material was filtered off and washed with water and ether, affording the title compound (2.40 g, 68%) as a brown solid. NMR showed a mixture of isomers (ca. 1:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05972935 |
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| Source dataset | uspto-grants-1999_10 |
|---|
| ORD ID | ord-215d83b5675643b88b411a9313bc44e4 |
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| Source note | uspto-grants-1999_10 |
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