Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 2-Amino-4-methylpyridine | HCID 1533 | — |
| Reactant | HCID 18331463 | HCID 18331463 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Catalyst | Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+) | HCID 15826098 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 18331456 | HCID 18331456 | 13.8% |
Reaction Steps
A mixture of 3-(di-(t-butoxycarbonyl)aminomethyl)bromobenzene (260 mg), tris(dibenzylideneacetone)dipalladium (42 mg), diphenylphosphinoferrocene (50 mg), potassium t-butoxide (102 mg), 2-amino-4-methylpyridine (108 mg) and toluene (10 ml) was heated under a nitrogen atmosphere at 80° C. for 22 h. Ethyl acetate and water were added to the reaction mixture. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=1:1) to give 29.2 mg of the titled compound (yield, 10%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06331553B1 |
|---|
| Source dataset | uspto-grants-2001_12 |
|---|
| ORD ID | ord-31a84c6f11cd44259832916072e8118e |
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| Source note | uspto-grants-2001_12 |
|---|
