HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 546374Generated: October 26, 2026
2-Bromopyridine → 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)but-3-yn-1-ol
https://huagongshe.com/reaction/546374
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Bromopyridine | HCID 7973 | — |
| Reactant | 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol | HCID 86643937 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-4-(pyridin-2-yl)but-3-yn-1-ol | HCID 67189118 | 43.6% |
Reaction Steps
To a round bottom flask were added 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol (0.47 g, 2.3 mmol), triethylamine (10 mL), 2-bromopyridine (0.28 mL, 2.7 mmol), bis(triphenylphosphine)palladium(II) dichloride (16 mg, 0.023 mmol) and copper(I) iodide (9 mg, 0.045 mmol). After this mixture was stirred with heating overnight at 60° C., it was allowed to cool to room temperature. The reaction was mixed directly with silica, concentrated and purified by silica chromatography to give the desired coupling product (286 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07935848B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-43f11b5f8d3d4467a492c2351b454c24 |
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| Source note | uspto-grants-2011_05 |
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