HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1021237Generated: October 29, 2026
Binap, (A+-)- → 1-[3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-4-(2-methylpyridin-4-yl)piperazine
https://huagongshe.com/reaction/1021237
Participants
| Role | Name | HCID | Charge |
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| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 1-(2-Methylpyridin-4-yl)piperazine | HCID 16762377 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | ((3-Bromo-2-fluorobenzyl)oxy)(tert-butyl)dimethylsilane | HCID 86686195 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 1-[3-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-4-(2-methylpyridin-4-yl)piperazine | HCID 86686210 | 66.3% |
Reaction Steps
[(3-Bromo-2-fluorobenzyl)oxy](tert-butyl)dimethylsilane (300 mg) was mixed with toluene (6 ml), and 1-(2-methylpyridin-4-yl)piperazine (200 mg), Pd2(dba)3 (43 mg), BINAP (88 mg), and sodium tert-butoxide (135 mg) were added thereto, followed by stirring at 80° C. for 5 hours. After cooling to room temperature, filtration was carried out by the addition of CHCl3 and Celite, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane/28% aqueous ammonia/MeOH/) to obtain 1-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-4-(2-methylpyridin-4-yl)piperazine (259 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08716470B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-933a972618514b4a84f729dfafa2cdb9 |
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| Source note | uspto-grants-2014_05 |
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