Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 2-Fluoro-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 49760512 | — |
| 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 66936939 | HCID 66936939 | 45.7% |
Reaction Steps
To a solution of 6-bromo-N-(3-fluorobenzyl)pyridin-2-amine (85 mg, 0.302 mmol) and 2-fluoro-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (102 mg, 0.430 mmol) in DME (2 mL) and 2M Na2CO3 aq (1 mL) was added PdCl2(dppf).CH2Cl2 adduct (21 mg, 0.026 mmol). This was then heated at 110° C. for 16 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′-fluoro-N-(3-fluorobenzyl)-5′-methyl-2,4′-bipyridin-6-amine (43 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08778951B2 |
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| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-ef3eafb7acff4d20a5ee1b95f7fbc411 |
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| Source note | uspto-grants-2014_07 |
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