Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Tris(furan-2-yl)phosphane | HCID 521585 | — |
| Reactant | 3-Formylfuran-2-boronic acid | HCID 3739337 | — |
| Reactant | S-(4-methylphenyl) 2-methyl-5-phenylpyridine-3-carbothioate | HCID 57722887 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57900077 | HCID 57900077 | — |
Reaction Steps
To a mixture of S-(4-methylphenyl) 2-methyl-5-phenylpyridine-3-carbothioate (66 mg, 0.20 mmol), Cu(I) thiophene-2-carboxylate (59 mg, 0.31 mmol), 3-formylfuran-2-boronic acid (31 mg, 0.22 mmol), Pd2dba3.CHCl3 (2 mg, 0.002 mmol), and tri-2-furylphosphine (1.4 mg, 0.006 mmol) was added THF (2.5 mL). The reaction mixture was heated to 50° C. for 15 h, cooled to room temperature, diluted with EtOAc, and washed with 1 N HCl and brine. The organic layer was concentrated and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 10.60 (s, 1H); 8.91 (s, 1H); 8.02 (s, 1H); 7.40-7.61 (series of m, 6H); 7.05 (s, 1H); 2.66 (s, 3H). LRMS (ESI) calc'd for C18H13NO3 [M+H]+, 292.1. found 292.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07790739B2 |
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| Source dataset | uspto-grants-2010_09 |
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| ORD ID | ord-6121ba9de4524940aceeb5ac71d793b5 |
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| Source note | uspto-grants-2010_09 |
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