Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Tolylboronic acid | HCID 79799 | — |
| Reactant | HCID 68900619 | HCID 68900619 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 69671732 | HCID 69671732 | 86.3% |
Reaction Steps
To a solution of 6-bromo-3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (100 mg, 0.329 mmol) in toluene (20 mL) and water (5 mL) was added 4-methylphenylboronic acid (67.1 mg, 0.493 mmol), Pd(PPh3)4 (18.4 mg, 0.016 mmol) and Cs2CO3 (55.3 mg, 0.658 mmol), and the reaction mixture was refluxed under Argon overnight. The mixture was filtered and the filtrate was washed with water (50 mL×2), dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified by column chromatography on silica gel (petroleum ether:ethyl acetate=1:1) to give the title compound (89.5 mg, 50.6% yield) as yellow solids. 1H NMR (DMSO-d6): 8.09 (m, 1H), 7.93 (dd, J=9.6 and 0.9 Hz, 1H), 7.77 (d, J=9.6 and 1.8 Hz, 1H), 7.64-7.58 (m, 4H), 7.33-7.28 (m, 3H), 7.19 (t, J=7.2 Hz, 1H), 3.85 (s, 3H), 2.35 (s, 3H). MS: m/z 316.2 [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-8790aa712bac45b5868f8ef6c5c99047 |
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| Source note | uspto-grants-2015_12 |
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