Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | (4-Methoxyphenyl)boronic acid | HCID 201262 | — |
| Reactant | HCID 68900619 | HCID 68900619 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 69671335 | HCID 69671335 | 84.5% |
Reaction Steps
A flask was charged with 6-bromo-3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (151 mg, 0.5 mmol), 4-methoxyphenylboronic acid (80 mg, 0.5 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 5.8 mg, 0.005 mmol), cesium carbonate (Cs2CO3, 326 mg, 1.0 mmol), 1,4-dioxane (10 mL) and water (2 mL). The mixture was stirred at 100° C. under Argon for 10 h. The mixture was evaporated to afford the crude product. The crude product was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=1:1) to give the title compound (140 mg, 84.2% yield) as yellow solids. 1H NMR (DMSO-d6): 8.06 (m, 1H), 7.90 (dd, J=9.5 and 0.9 Hz, 1H), 7.75 (dd, J=9.6 and 1.8 Hz, 1H), 7.67-7.62 (m, 4H), 7.32 (d, J=8.1 Hz, 1H), 7.19 (t, J=7.5 Hz, 1H), 7.03 (d, J=8.7 Hz, 2H), 3.85 (s, 3H), 3.80 (s, 3H). MS: m/z 332.2 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09199983B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-153eb772d33a4628b77518fec5bd2762 |
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| Source note | uspto-grants-2015_12 |
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