HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → HCID 58127193, compound
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 | 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 | Methanol | HCID 887 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58127193 | HCID 58127193 | — |
Reaction Steps
A mixture of 6-bromo-N-(3-fluorobenzyl)pyridin-2-amine (A, 2.0 g, 7.11 mmol), 5-chloro-2-fluoropyridin-4-ylboronic acid (2.0 g, 11.4 mmol), PdCl2(dppf).CH2Cl2 adduct (0.465 g, 0.569 mmol), DME (27 mL) and 2M aqueous Na2CO2 (9.25 mL, 18.50 mmol) was stirred at about 100° C. for 3 hr. After cooling to ambient temperature, the mixture was diluted with EtOAc (25 mL) and MeOH (20 mL), filtered, and concentrated in vacuo to yield a crude material. The crude material was purified by column chromatography [silica gel, 120 g, EtOAc/hexane=0/100 to 20/80] providing 5′-chloro-2′-fluoro-N-(3-fluorobenzyl)-2,4′-bipyridin-6-amine (1.26 g) as an off-white solid. LCMS (m/z): 332.2 [M+H]+; Retention time=0.92 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415381B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-99b79bc360214d3b93f04821d4387dad |
| Source note | uspto-grants-2013_04 |