Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | 2-Chloro-5-(1-methylethyl)pyridine | HCID 10866575 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | 2-(Dicyclohexylphosphino)biphenyl | HCID 2734216 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 17985541 | HCID 17985541 | 37,637% |
Reaction Steps
Dissolve 2-chloro-5-isopropylpyridine (5 g, 0.032 mol), benzylamine (6.8 g, 0.064 mmol), Biphenyl-2-yl-dicyclohexyl-phosphine (0.46 g, 1.3 mmol), Pd(OAc)2 (0.14 g, 0.64 mmol), and sodium tert-butoxide (4.3 g, 0.045 mol) in 60 mL of toluene. Deoxygenate three times. Heat at 100° C. for 18 hours. Cool and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 1:1 hexanes:ethyl acetate to provide 5.5 g of the desired compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08022065B2 |
|---|
| Source dataset | uspto-grants-2011_09 |
|---|
| ORD ID | ord-90035964792a4fbd8e34e4d45ac9d333 |
|---|
| Source note | uspto-grants-2011_09 |
|---|
