HuagongsheHuagongshe Chemistry Print Report · For research reference only
(6-Decyloxy-2-fluoropyrid-3-yl)boronic acid → 2-(6-Decyloxy-2-fluoropyrid-3-yl)-5-phenyl-1,3,4-thiadiazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (6-Decyloxy-2-fluoropyrid-3-yl)boronic acid | HCID 11044681 | — |
| Reactant | 2-Bromo-5-phenyl-1,3,4-thiadiazole | HCID 13104117 | — |
| Catalyst | Ethanol | HCID 702 | — |
| Catalyst | Water | HCID 962 | — |
| Catalyst | Toluene | HCID 1140 | — |
| Catalyst | Sodium Carbonate | HCID 10340 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | 2-(6-Decyloxy-2-fluoropyrid-3-yl)-5-phenyl-1,3,4-thiadiazole | HCID 22104433 | 82% |
Reaction Steps
(6-Decyloxy-2-fluoropyrid-3-yl)boronic acid (3.7 g, 12.4 mmol) and 2-bromo-5-phenyl-1,3,4-thiadiazole (1.0 g, 4.15 mmol) are refluxed for 6 hours in a mixture of sodium carbonate (3.95 g), toluene (50 ml), ethanol (25 ml) and water (25 ml) and tetrakis(triphenylphosphine)palladium(0) (5 mol %) as catalyst. Aqueous work-up and column chromatography (SiO2, CH2C12) give 1.4 g (82% of theory) of 2-(6-decyloxy-2-fluoropyrid-3-yl)-5-phenyl-1,3,4-thiadiazole.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05847149 |
| Source dataset | uspto-grants-1998_12 |
| ORD ID | ord-555aab7bbc724e25b0b7fbe83ad81823 |
| Source note | uspto-grants-1998_12 |