HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 58235212, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 3-Bromo-5-hydroxypyridine | HCID 599529 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58235212 | HCID 58235212 | — |
Reaction Steps
The title compound is synthesized according to general procedure GP2 starting from 2.0 g (11.6 mmol) 5-bromo-3-hydroxy-pyridine and 2.3 mL (16.2 mmol) 1-trimethylsilyl-ethyne using 66 mg (0.3 mmol) CuI, 303 mg (1.2 mmol) triphenylphosphine, 243 mg (0.3 mmol) PdCl2(PPh3)2 and 19 mL (139 mmol) triethylamine in 20 mL dry THF. For the work-up the reaction mixture is diluted with ethyl acetate and small amounts of cyclohexane, the organic phase is extracted with water and brine. The product is purified by chromatography on silica gel using a DCM/MeOH gradient. Yield: 2.0 g (91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08916548B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-a7a7511a7b6647bb82d663bfa6b7c149 |
| Source note | uspto-grants-2014_12 |