Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N-Methylpropylamine | HCID 12315 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 86615009 | HCID 86615009 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 68816506 | HCID 68816506 | 63.2% |
Reaction Steps
Add methylpropylamine (0.21 mL, 2.0 mmol) to a suspension of 2-chloro-6-methanesulfonyl-isonicotinic acid methyl ester (0.25 g, 1.0 mmol), palladium acetate (0.022 g, 0.1 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.062 g, 0.1 mmol), and cesium carbonate (0.325 g, 1.0 mmol) in toluene (5 mL) at room temperature and stir 18 h at 80° C. Cool, filter through a filtering agent and purify (silica gel chromatography, eluting with 20:80 to 40:60 ethyl acetate:hexanes) to give the title compound (0.181 g, 63%).
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-aa78343b32ed46ec8e820e2172def4f1 |
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| Source note | uspto-grants-2009_11 |
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