Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (3-Chlorophenyl)boronic acid | HCID 2734323 | — |
| Reactant | 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One | HCID 73712352 | — |
| Solvent | Dimethoxyethane ethanol water | HCID 86587095 | — |
| Product | HCID 73712349 | HCID 73712349 | 13.8% |
Reaction Steps
Into a dry microwave vial under N2 was added 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(PPh3)Cl2 (about 1 mol %), and Cs2CO3 (17.8 mg, 0.0547 mmol) in DME/H2O/EtOH (7/3/2, 0.5 mL). 3-Chlorophenyl boronic acid (6.3 mg, 0.046 mmol) was added and the solution was heated in the microwave for 5 minutes at 160° C., filtered, and was purified by Prep HPLC to give 3 mg (11%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 469 (M−H)+; 1H NMR (300 MHz, DMSO) δ ppm 1.84-1.91 (m, 2H), 2.25 (br d, 2H), 3.16-3.23 (m, 2H), 3.61 (br d, 2H), 3.84-4.01 (m, 3H), 5.43 (s, 1H), 6.37-6.43 (m, 1H), 6.89 (d, 1H), 7.34-7.94 (m. 12H), 8.41 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06921821B2 |
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| Source dataset | uspto-grants-2005_07 |
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| ORD ID | ord-b13d743577304cdc9349665a08cbab35 |
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| Source note | uspto-grants-2005_07 |
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