Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pivalic acid | HCID 6417 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1,2-Dimethylimidazole | HCID 15617 | — |
| Reactant | 6-Bromo-2-methoxypyridin-3-amine | HCID 10536137 | — |
| Reactant | Tri(cyclohexyl)phosphine tetrafluoroborate | HCID 20066521 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 89995597 | HCID 89995597 | 35% |
Reaction Steps
Palladium acetate (5.5 mg, 0.025 mmol) was added to a solution of 6-bromo-2-methoxypyridin-3-amine (25 mg, 0.123 mmol), 1,2-dimethyl-1H-imidazole (35.5 mg, 0.369 mmol), pivalic acid (3.8 mg, 0.037 mmol), tricyclohexylphosphine tetrafluoroborate salt (18.1 mg, 0.049 mmol) and potassium carbonate (25.5 mg, 0.185 mmol) in DMA (410 μL). The reaction mixture was heated under microwave irradiation at 120° C. for 1 hour. The reaction was diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The crude mixture was purified by Biotage silica gel column chromatography eluting with 1 to 5% MeOH/aq. NH3 (10/1) in DCM to afford the title compound as a white solid (9 mg, 35%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409907B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-a5794beed83143719ab4496183baf3f3 |
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| Source note | uspto-grants-2016_08 |
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