HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 220442Generated: October 30, 2026
Potassium Phosphate, Tribasic → 4-[2-(4-Fluorophenyl)-pyridin-3-yl]-piperazine-1-carboxylic acid t-butyl ester
https://huagongshe.com/reaction/220442
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | 3-(4-BOC-piperazino)-2-chloropyridine | HCID 59321836 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Catalyst | Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene | HCID 129828017 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 4-[2-(4-Fluorophenyl)-pyridin-3-yl]-piperazine-1-carboxylic acid t-butyl ester | HCID 68722827 | 28% |
Reaction Steps
Dissolve 4-(2-chloropyridin-3-yl)-piperazine-1-carboxylic acid t-butyl ester (2.7 g, 9.1 mmol) in toluene (30 mL). Add 4-fluorophenylboronic acid (1.92 g, 13.70 mmol) followed by bis(dibenzylideneacetone)palladium(0) (0.42 g, 0.46 mmol), 1,2,3,4,5-pentaphenyl-1′-(di-t-butylphosphino)ferrocene (CTC-Q-PHOS) (0.65 g, 0.91 mmol) and potassium phosphate (5.8 g, 27.3 mmol). Heat the reaction mixture at 100° C. for 23 hr. Cool to room temperature, concentrate and partition the residue between ethyl acetate and 1 N sodium hydroxide (pH=11). Dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes), to give 4-[2-(4-fluorophenyl)-pyridin-3-yl]-piperazine-1-carboxylic acid t-butyl ester (28%). MS (ES): m/z=358 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08202873B2 |
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| Source dataset | uspto-grants-2012_06 |
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| ORD ID | ord-442e3914cfbc4e5b9d3a867ccfc19ef0 |
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| Source note | uspto-grants-2012_06 |
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