Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | (2-Chloro-5-methoxypyridin-4-yl)boronic acid | HCID 46738707 | — |
| Reactant | 6-bromo-N-(3-fluorobenzyl)pyridin-2-amine | HCID 58127376 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Product | HCID 86650643 | HCID 86650643 | 7.8% |
Reaction Steps
To a solution of 6-bromo-N-(3-fluorobenzyl)pyridin-2-amine (555 mg, 1.974 mmol) and 2-chloro-5-methoxypyridin-4-ylboronic acid (518 mg, 2.76 mmol) in DME (4 ml) and 2M Na2CO3 aq (2 ml) was added PdCl2(dppf).CH2Cl2 adduct (81 mg, 0.099 mmol). This was then heated at 110° C. for 5 h. The reaction mixture was allowed to cool and then the DME was evaporated under reduced pressure. The resulting residue was partitioned between EtOAc and water. The organics were combined, then washed with H2O (×3), saturated aq. brine (×3), then dried (Na2SO4), filtered and evaporated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel; 15% to 25% EtOAc/hexane) to give 2′-chloro-N-(3-fluorobenzyl)-5′-methoxy-2,4′-bipyridin-6-amine (53 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08778951B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-48c994532d3d48eda44610a2ab68197a |
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| Source note | uspto-grants-2014_07 |
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