Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Methyl 2-chloropyridine-4-carboxylate | HCID 2736842 | — |
| Reactant | 2-Butanamine, (S)- | HCID 6713753 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 68814422 | HCID 68814422 | — |
Reaction Steps
Degas with nitrogen a suspension containing 2-chloro-isonicotinic acid methyl ester (2.15 g, 12.5 mmol), palladium acetate (281 mg, 1.25 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (780 mg, 1.25 mmol), cesium carbonate (4.95 g, 15 mmol), and (S)-sec-butylamine (1.5 mL, 15 mmol) in toluene (30 mL) and heat in a sealed tube at 90° C. overnight. Cool to room temperature and filter the solids through a filtering agent. Wash with ethyl acetate (30 mL), concentrate and purify (silica gel chromatography, eluting with 15:85 to 30:70 ethyl acetate:hexanes) to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07618978B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-6ff3efd3ffc34664b883efad7607a085 |
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| Source note | uspto-grants-2009_11 |
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