HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Phosphate, Tribasic → 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Reactant | 3-Methoxy-4-(methoxycarbonyl)benzeneboronic acid | HCID 17750256 | — |
| Reactant | 5-(4-Chloro-2-ethyl-pyridin-3-ylethynyl)-pyridin-2-ylamine | HCID 58235313 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid methyl ester | HCID 58235311 | — |
Reaction Steps
The title compound is synthesized according to general procedure GP3 starting from 1.5 g (5.0 mmol) 5-(4-Chloro-2-ethyl-pyridin-3-ylethynyl)-pyridin-2-ylamine (A-30) using 1.6 g (7.4 mmol) 3-methoxy-4-methoxycarbonylphenyl boronic acid, 135 mg (0.15 mmol) Pd2(dba)3, 354 mg (0.74 mmol) X-Phos and 2.2 g (9.4 mmol) K3PO4 in 20 mL dioxane. The reaction mixture is stirred under reflux over night. The solvent is removed under reduced pressure before water is added and the formed precipitate is collected by filtration. The product is purified by chromatography on silica gel using a DCM/MeOH-gradient. Yield: 1.07 g (56%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09090564B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-cd6ba0b87096456d83731071af1c7d4e |
| Source note | uspto-grants-2015_07 |