Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 58459292 | HCID 58459292 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67431344 | HCID 67431344 | — |
Reaction Steps
To a microwave vial was added cesium carbonate (1.30 g, 3.98 mmol), Pd2(dba)3 (0.146 g, 0.159 mmol), Xantphos (0.230 g, 0.398 mmol), N-(1-(1-(5-bromopyridin-3-yl)-6-fluoro-1H-benzo[d]imidazol-2-yl)ethyl)acetamide (0.600 g, 1.59 mmol), and methanesulfonamide (0.166 g, 1.75 mmol) in dioxane (7.95 mL). The suspension was purged with nitrogen for 5 min then was stirred at 120° C. for 3 h under microwave irradiation. The solution was loaded directly onto silica gel then purified by MPLC (eluted with a gradient of 0-10% MeOH in DCM) to afford N-(1-(6-fluoro-1-(5-(methylsulfonamido)pyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethyl)acetamide as an off-white solid. LC-MS (ESI) m/z 392.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575183B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-e7a0ecf519c44fa799c222fef191cd43 |
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| Source note | uspto-grants-2013_11 |
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