HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2059793Generated: November 1, 2026
Trimethylsilylacetylene → Tert-butyl (5-((trimethylsilyl)ethynyl)thiazol-2-yl)carbamate
https://huagongshe.com/reaction/2059793
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | tert-butyl N-(5-bromo-1,3-thiazol-2-yl)carbamate | HCID 21300388 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl (5-((trimethylsilyl)ethynyl)thiazol-2-yl)carbamate | HCID 45117882 | 86% |
Reaction Steps
A mixture of tert-butyl (5-bromo-1,3-thiazol-2-yl)carbamate (2.79 g, 10 mmol), ethynyltrimethylsilane (1.27 g, 13 mmol), Pd(PPh3)4 (578 mg, 0.5 mmol), CuI (143 mg, 0.75 mmol), and diisopropylethylamine (1.94 g, 15 mmol) in DMF (10 mL) was heated at 50° C. overnight under an atmosphere of N2. Upon cooling to ambient temperature, the reaction mixture was concentrated and the crude product was purified by silica gel flash chromatography (eluted with 20% EtOAc/hexanes) to give a yellow solid (2.55 g, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08278307B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-fd307c3e74af4021ba605482376db853 |
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| Source note | uspto-grants-2012_10 |
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