HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 44612467, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Isoquinolin-3-Amine | HCID 311869 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 58285186 | HCID 58285186 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 44612467 | HCID 44612467 | — |
Reaction Steps
1-(2-Chloro-pyridin-4-ylmethyl)-4-(N,N-dimethylcarbamoyl)piperazine (1.0 equiv) (Preparation B-12) was mixed with 3-aminoisoquinoline (1.0 equiv), Pd2(dba)3(0.1 equiv), xantphos (0.15 equiv), and Cs2CO3 (1.4 equiv) in toluene. The mixture was refluxed overnight, and EtOAc was added in to dilute the mixture. After filtration, the filtrate was concentrated and applied onto a silica gel column. The title compound was obtained as a yellow solid (50 mg, 22% yield): 1H NMR (CDCl3, 300 MHz) δ: 2.47 (t, J=5.0 Hz, 4H, PyridylCH2NCH2CH2), 2.83 (d, J=4.8 Hz, 3H, NHCH3), 3.41 (t, J=5.0 Hz, 4H, NCH2CO), 3.51 (s, 2H, pyridylCH2), 6.86-8.99 (m, 9H, isoquinolyl+pyridyl).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08461339B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-521ba77a277d4f6f93bf7d7336da25df |
| Source note | uspto-grants-2013_06 |