Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Chlorophenylboronic acid | HCID 74299 | — |
| Reactant | HCID 67287330 | HCID 67287330 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67289726 | HCID 67289726 | 57% |
Reaction Steps
Ethyl 7-(4-(5-bromopyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (50 mg, 0.094 mmol), 4-chlorophenylboronic acid (15 mg, 0.094 mmol), Na2CO3 (25 mg, 0.24 mmol) and Pd(PPh3)4 (11 mg, 0.0094 mmol) were placed in a 1 mL vial and diluted with toluene (800 μL) and water (80 μL). The vial was purged with argon, sealed and heated to 100° C. After stirring for 36 hours, the reaction was loaded onto silica gel eluting with 5% ethyl acetate/hexanes to 70% ethyl acetate/hexanes to yield the desired compound (30 mg, 0.053 mmol, 57% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08785445B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-7427f9b79ad54de989dddb313218fdc4 |
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| Source note | uspto-grants-2014_07 |
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