HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 3-iodo-4-(3-methyl-but-2-enylamino)-benzoate → Methyl 3-(propan-2-yl)-1H-indole-5-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 3-iodo-4-(3-methyl-but-2-enylamino)-benzoate | HCID 22663311 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Methyl 3-(propan-2-yl)-1H-indole-5-carboxylate | HCID 22663178 | 79.4% |
Reaction Conditions
| Temperature | 110 °C |
|---|
Reaction Steps
A solution of methyl 3-iodo-4-(3-methyl-but-2-enylamino)-benzoate (2.0 g, Reference Example 53) in triethylamine (1.6 ml) and acetonitrile (35 ml) was treated with palladium acetate (0.05 g). The mixture was sealed in a bomb and heated at 110° C. for 18 hours. After cooling the reaction mixture was filtered and the filtrate was evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and petroleum ether (1:4, v/v) to give the title compound (1.0 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07329675B2 |
| Source dataset | uspto-grants-2008_02 |
| ORD ID | ord-b693bcd304404fb7a7fa0ac757f5de9b |
| Source note | uspto-grants-2008_02 |