HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 549944Generated: October 26, 2026
1-Bromonaphthalene → tert-Butyl 4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate
https://huagongshe.com/reaction/549944
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Bromonaphthalene | HCID 7001 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | Tert-butyl 4-{4-[(trimethylsilyl)ethynyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate | HCID 67157073 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-Butyl 4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate | HCID 67157278 | — |
Reaction Steps
Tetrakis(triphenylphosphine)palladium(0) (95 mg), copper(I) iodide (31 mg) and triethylamine (200 mg) are added to a solution of tert-butyl 4-{4-[(trimethylsilyl)ethynyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (XI-1, 600 mg) and 1-bromonaphthalene (375 mg) in degassed N,N-dimethylformamide. After heating to 85° C., tetra-n-butylammonium fluoride (1M in THF, 1.81 ml) is added dropwise. The reaction mixture is then diluted with water and extracted with ethyl acetate. The organic extracts are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives tert-butyl 4-[4-(naphthalen-1-ylethynyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (576 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07943774B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-7b555b457fe94adfac93aae15ac2cc7a |
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| Source note | uspto-grants-2011_05 |
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