Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | (5-Chloro-2-fluoropyridin-4-yl)boronic acid | HCID 44754822 | — |
| Reactant | HCID 58127318 | HCID 58127318 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58127300 | HCID 58127300 | 77.2% |
Reaction Steps
A mixture of 6-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)-3-(trifluoromethyl)pyridin-2-amine (100 mg, 0.339 mmol), 5-chloro-2-fluoropyridin-4-ylboronic acid (89 mg, 0.509 mmol), PdCl2(dppf). CH2Cl2 adduct (27.7 mg, 0.034 mmol), DME (1.5 mL) and 2M aqueous Na2CO2 (0.5 mL, 1 mmol) was stirred in a sealed glass vessel at about 100° C. for about 3 hours. After cooling to ambient temperature the mixture was diluted with EtOAc (25 mL) and MeOH (20 mL), filtered and concentrated in vacuo. The resulting crude material was purified by column chromatography [silica gel, 12 g, EtOAc/hexane=5/100 to 50/50] to yield 5′-chloro-2′-fluoro-N-((tetrahydro-2H-pyran-4-yl)methyl)-5-(trifluoromethyl)-2,4′-bipyridin-6-amine (Intermediate T, 102 mg, 77%). LCMS (m/z): 390.2 [M+H]+; Retention time=1.12 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08415381B2 |
|---|
| Source dataset | uspto-grants-2013_04 |
|---|
| ORD ID | ord-57606b5b3d7e449da4b916cd23a4439f |
|---|
| Source note | uspto-grants-2013_04 |
|---|
