HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 7-Chloro-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)isoquinolin-3-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 7-Chloroisoquinolin-3-amine | HCID 23321168 | — |
| Reactant | 2-Chloro-4-(pyrrolidin-1-ylmethyl)pyridine | HCID 58113871 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 7-Chloro-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)isoquinolin-3-amine | HCID 44596293 | 32% |
Reaction Steps
Pd2(dba)3(102 mmg, 0.11 mmol) and xantphos (92 mg, 0.16 mmol) were added to a solution of 7-chloroisoquinolin-3-amine (200 mg, 1.12 mmol) (Preparation C-9), 2-chloro-4-pyrrolidin-1-ylmethyl-pyridine (220 mmg, 1.12 mmol) (Preparation B-11) and Cs2CO3 (500 mg, 1.53 mmol) in toluene (50 mL). The suspension was heated under reflux overnight, and THF (50 mL) was added in to dilute the mixture. After filtration, the filtrate was concentrated. The crude material was further purified by silica gel chromatography (EtOAc/Hexane=1/1) and afforded the title compound (120 mg, 32% yield) as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08461339B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-cb67fe8c1d0546d99d6ff28907c2e0d8 |
| Source note | uspto-grants-2013_06 |