HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 4-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (2-Methoxypyridin-4-yl)boronic acid | HCID 23546919 | — |
| Reactant | 2-Bromo-4-chloro-1-[2-(trimethylsilyl)ethynyl]benzene | HCID 102078595 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-{5-Chloro-2-[(trimethylsilyl)ethynyl]phenyl}-2-methoxypyridine | HCID 123388929 | — |
Reaction Steps
A solution of 333 mg (1.16 mmol) of [(2-bromo-4-chlorophenyl)ethynyl](trimethyl)silane, 195 mg (1.28 mmol, 1.1 eq.) of (2-methoxypyridin-4-yl)boronic acid, 401 mg (2.9 mmol, 2.5 eq.) of potassium carbonate and 14 mg (0.02 mmol, 0.015 eq.) of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/monodichloromethane adduct in 18 ml of dioxane was irradiated in a microwave at 130° C. for 15 min. The reaction mixture was then filtered through Celite and the residue was washed with dioxane. The combined filtrates were concentrated under reduced pressure. After addition of water/ethyl acetate and phase separation, the organic phase was concentrated under reduced pressure. Yield: 550 mg (purity 41%, 62% of theory)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09434690B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-9bdb4e2f02ed4cfaba6cf5dfe78e68af |
| Source note | uspto-grants-2016_09 |