Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | HCID 58095189 | HCID 58095189 | — |
| Reactant | N-(4-(trimethylstannyl)pyridin-2-yl)acetamide | HCID 59529632 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58095104 | HCID 58095104 | 10.3% |
Reaction Steps
Methyl 2-[5-bromo-4-cyano-3-(2,4-dichlorophenyl)-2-thienyl]-1H-imidazole-5-carboxylate (0.216 g, 0.472 mmol), N-[4-(trimethylstannyl)pyridin-2-yl]acetamide (0.170 g, 0.567 mmol), lithium chloride (0.0601 g, 1.42 mmol), copper(I) iodide (0.0270 g, 0.142 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.0273 g, 0.0236 mmol) were combined in dioxane (10 mL) under an atmosphere of Argon. The solution was heated at 110° C. for 3 hours. The solvent was evaporated, and column chromatography was performed to yield the title compound (0.0250 g, 10%). LCMS: (FA) ES+ 513. 1H NMR (300 MHz, d6-DMSO) 8.59-8.57 (m, 1H), 8.54-8.50 (m, 1H), 7.88-7.82 (m, 2H), 7.61-7.58 (m, 2H), 7.56-7.52 (m, 1H), 3.75 (s, 3H), 2.13 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08796314B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-6f9acae9a5484d98804cde2fe8775ec7 |
|---|
| Source note | uspto-grants-2014_08 |
|---|