Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Bromopyridine | HCID 12286 | — |
| Reactant | HCID 178515914 | HCID 178515914 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178506184 | HCID 178506184 | 18.2% |
Reaction Steps
4-(5-{[3-(trifluromethyl)phenyl]amino}-4H-1,2,4-triazol-3-yl)phenol (100 mg, 0.31 mmol) was dissolved in 2 mL of anhydrous DMF in 2-5 mL microwave vial (Personal Chemistry). Solid Cs2CO3 (203.4 mg, 0.62 mmol) was added, followed by 3-bromopyridine (74.0 mg, 0.468 mmol). The vial was capped and microwaved at 250° C. for 30 min. Then ca. 1 mL of MeOH was added to dissolve the formed suspension. The resulting reddish-brown solution was filtered through 0.22 u syringe filter and purified by reverse phase preparative HPLC using acetontrile/water system with 0.01% of TFA. The fractions, containing the product, were collected and partitioned between EtOAc and saturated aqueous NaHCO3. Ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate and filtered. Solvent was removed in vacuo to give the title compound as a yellow solid (22.4 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07652051B2 |
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| Source dataset | uspto-grants-2010_01 |
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| ORD ID | ord-1a8c91b033d64389adc50b18c17bde3d |
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| Source note | uspto-grants-2010_01 |
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