Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 2-Butanamine, (S)- | HCID 6713753 | — |
| Reactant | HCID 86615002 | HCID 86615002 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 68816237 | HCID 68816237 | 81% |
Reaction Steps
Add 2-chloro-6-propanesulfonyl-isonicotinic acid methyl ester (2.70 g, 9.71 mmol), toluene (40 mL), palladium acetate (218 mg, 0.97 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (605 mg, 0.97 mmol), cesium carbonate (4.75 g, 14.6 mmol), and (S)-sec-butylamine (1.46 mL, 14.6 mmol) to a sealed vessel flushed with nitrogen. Heat and stir the sealed vessel at 90° C. overnight. Cool to room temperature, filter through a pad of filtering agent, concentrate and purify (silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes) to give the title compound (2.47 g, 81%).
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-1ab1ad85591045078f9c73cf61a6277d |
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| Source note | uspto-grants-2009_11 |
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