HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 606884Generated: October 25, 2026
3-Bromo-5-methoxypyridine → 3-(4-Fluoro-3-methylphenylethynyl)-5-methoxypyridine
https://huagongshe.com/reaction/606884
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Bromo-5-methoxypyridine | HCID 817163 | — |
| Reactant | 4-Ethynyl-1-fluoro-2-methylbenzene | HCID 16213797 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Diisopropylamine | HCID 7912 | — |
| Product | 3-(4-Fluoro-3-methylphenylethynyl)-5-methoxypyridine | HCID 67047453 | 51.1% |
Reaction Steps
Dissolve 3-bromo-5-methoxypyridine (1.0 g, 5.35 mmol) in diisopropylamine (17 mL) and toluene (10 mL) under nitrogen. Add tetrakis(triphenylphosphine)palladium (0.200 g, 0.16 mmol). Heat at 60° C. and add 4-ethynyl-1-fluoro-2-methylbenzene (717 mg, 5.35 mmol) and copper (I) iodide (20 mg, 0.11 mmol). After 20 h add additional 4-ethynyl-1-fluoro-2-methylbenzene (100 mg, 0.75 mmol) and heat at 60° C. for 5 h. Concentrate and purify using silica gel chromatography, eluting with 30:70 to 40:60 ethyl acetate:hexanes, to give the title compound (660 mg, 51%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07915424B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-f3df2be9dc0a47619caf9aebe8412b39 |
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| Source note | uspto-grants-2011_03 |
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