Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Benzenamine, 4-(4-morpholinyl)- | HCID 75655 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 71469141 | HCID 71469141 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 71469142 | HCID 71469142 | — |
Reaction Steps
N-(3-(2-Chloro-5-(phenylamino)pyrimidin-4-yl)phenyl)acrylamide (30 mg, 0.086 mmol), 4-morpholinoaniline (15.24 mg, 0.086 mmol) and Cs2CO3 (33.4 mg, 0.103 mmol) were dissolved in toluene (4.5 mL) in a sealable microwave compatible reaction tube, then tris(dibenzylideneacetone)-dipalladium(0) (Pd2(dba)3; 1.566 mg, 1.710 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (1.979 mg, 3.42 μmol) were added. The reaction tube was sealed and the reaction was heated under microwave irradiation (30 min, 200° C., 3 atm). After completion of the reaction, solvent was removed by vacuum and product was purified by flash column chromatography. 1H NMR (400 MHz, CD3OD): δ 8.32 (s, 1H), 8.21 (s, 1H), 7.69-7.61 (m, 4H), 7.30 (t, 1H, J=8.0 Hz), 7.07 (m, 2H), 6.95 (m, 2H), 6.65 (m, 3H), 6.42-6.37 (m, 2H), 5.76 (dd, 1H, J=2.4 and 9.6 Hz), 3.82 (m, 4H), 3.08 (m, 4H); ESI-MS: [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08703767B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-d394102efcc648998648c737eec4fa95 |
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| Source note | uspto-grants-2014_04 |
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