Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5-Bromopyridine-2-carbaldehyde | HCID 9877562 | — |
| Reactant | N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine | HCID 58456089 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 131735917 | HCID 131735917 | — |
Reaction Steps
A mixture of 5-bromopyridine-2-carbaldehyde (500 mg, 2.69 mmol), N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (1.23 g, 3.24 mmol), PdCl2(dppf) (216 mg, 0.295 mmol), sodium carbonate (2 M, 2.70 mL, 5.40 mmol), and dioxane (10.0 mL) was evacuated and purged with Ar(g) (3×), and then irradiated under microwave at 100° C. for 10 minutes. The mixture was filtered, diluted with ethyl acetate and washed with water. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (25% ethyl acetate in hexanes) to afford 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carbaldehyde. C18H14F3N4O [M+H]+ 359. found 359.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09376418B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-f6deffd9d1c7485fbd1d097558eef0c4 |
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| Source note | uspto-grants-2016_06 |
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