Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 4-Amino-3-methoxybenzamide | HCID 53923798 | — |
| Reactant | HCID 86726465 | HCID 86726465 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86726474 | HCID 86726474 | 60% |
Reaction Steps
To a degassed mixture of 2-chloro-4-isopropoxy-7-((2-(trimethylsilyl)ethoxy)methyl)-5-(4-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-imidazol-2-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), 4-amino-3-methoxybenzamide (1.2 equiv) and cesium carbonate (3.0 equiv) in 1,4-dioxane (0.07 M) was added palladium acetate (0.1 equiv) and 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (0.3 equiv). The reaction was stirred at 100° C. for 3 h. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-2% DCM in MeOH) to afford the crude title compound (60% yield) as a yellow solid. MS (ESI) m/z 758.2 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428509B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-1275aa09ab8b4509a64ffec4394a7f09 |
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| Source note | uspto-grants-2016_08 |
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