HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 66705970, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 5-Bromo-N-ethylpyridin-2-amine | HCID 22504916 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66705970 | HCID 66705970 | — |
Reaction Steps
The title compound is synthesized according to general procedure GP2 starting from 909 mg (4.5 mmol) 5-bromo-2-ethylamino-pyridine and 0.89 mL (6.3 mmol) 1-trimethylsilyl-ethyne using 26 mg (0.13 mmol) CuI, 118 mg (0.45 mmol) triphenylphosphine, 82 mg (0.12 mmol) PdCl2(PPh3)2 and 6.3 mL (45.0 mmol) triethylamine in 7 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 hexane/ethyl acetate gradient. Yield: 980 mg (99%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618111B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-3f8ffb04704247aa80cb0f95fdb0b1ac |
| Source note | uspto-grants-2013_12 |