Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-(Methylsulfonyl)phenylboronic acid | HCID 2773542 | — |
| Reactant | HCID 57941069 | HCID 57941069 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 11554963 | HCID 11554963 | 50.7% |
Reaction Steps
To a solution of (6′-chloro-3,4,5,6-tetrahydro-2H[1,4′]bipyridinyl-2′-yl)-(4-trifluoromethoxyphenyl)-amine (200 mg, 0.53 mmol) in 1,4-dioxane (8 mL) were added sodium carbonate (1N solution; 228 mg, 2.12 mmol), and tetrakis(triphenylphosphine) palladium(0) (62 mg, 0.053 mmol), followed by 3-(methanesulphonyl)-phenyl boronic acid (215 mg, 1.06 mmol). This reaction mixture was refluxed for 12 hours, after which time water was added (10 mL) to the reaction mixture, and the product was extracted with ethyl acetate. The organic layer was dried over sodium sulphate, filtered, and the filtrate was concentrated under vacuum. The resulting product was purified through column chromatography using 230-400 mesh silica gel (15% ethyl acetate in petroleum ether) to afford the desired compound as a colorless solid (132 mg, yield 50%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07622486B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-9ec183314cbf4e5db0cdc06650cbfa83 |
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| Source note | uspto-grants-2009_11 |
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