HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → HCID 12216708, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Dimethyl 5-iodoisophthalate | HCID 2758568 | — |
| Reactant | 6-Phenyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane | HCID 16119965 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 12216708 | HCID 12216708 | 59% |
Reaction Steps
To dimethyl 5-iodoisophthalate (Matrix Scientific, 800 mg, 2.5 mmol) in THF (20 ml), 2-pyridine boronic acid N-phenyldiethanol amine ester (Aldrich, 1.8 g, 6.6 mmol), K2CO3 (912 mg, 6.6 mmol), triphenyl phosphine (173 mg, 0.66 mmol) were added followed by Pd(OAc)2 and cuprous iodide (251 mg, 1.32 mmol). After refluxing for 24 h, reaction mixture was filtered through a pad of celite. Residual solvent was evaporated on a rotavap under reduced pressure and the crude was dissolved in ethyl acetate. Insoluble material was filtered off and the remaining residue was evaporated to dryness and column purified (60% ethylacetate/40% hexanes) to yield 400 mg of dimethyl 5-(pyridin-2-yl)isophthalate as yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08299267B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-d0f8cf0b2f6c4592bfed023d7a90adfc |
| Source note | uspto-grants-2012_10 |