HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Ethyl 5-((trimethylsilyl)ethynyl)nicotinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Ethyl 5-bromopyridine-3-carboxylate | HCID 140785 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Ethyl 5-((trimethylsilyl)ethynyl)nicotinate | HCID 67047749 | 86% |
Reaction Steps
A solution of ethyl-5-bromonicotinate (30 g, 130.40 mmol), triethylamine (78 mL) and ethyl acetate (130 mL) is degassed for 15 min. Add trimethylsilylacetylene (88.46 mL, 625.92 mmol), bis(triphenylphosphine)palladium (II) dichloride (4.57 g, 6.52 mmol) and copper (I) iodide (0.25 g, 1.30 mmol) and stir at 50° C. under-nitrogen for 16 h. Cool to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with 10:1 hexanes:ethyl acetate, to give the title compound (27.7 g, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07915424B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-6b54da0751cb4c979b9b53d0c5f2c2c5 |
| Source note | uspto-grants-2011_03 |