HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 5-(4-Chlorophenyl)pyridin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Amino-5-bromopyridine | HCID 70622 | — |
| Reactant | 4-Chlorophenylboronic acid | HCID 74299 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | 5-(4-Chlorophenyl)pyridin-2-amine | HCID 13242644 | 78% |
Reaction Steps
2-Amino-5-bromopyridine (2) was reacted with 4-chlorophenylboronic acid (3) in dioxane/water in the presence of 2.2 equivalents of Na2CO3 and 1 mol % Pd(OAc)2 plus 1 mol % PdCl2(dppf).CH2Cl2 at 90° C. for 1.5 h. After cooling to room temperature the product (4) was precipitated as the HCl salt by adding HCl (25%, 6 equiv) followed by removal of dioxane under vacuum. The salt was filtered, digested in diethylether, filtered and then converted to the free amine by treatment with aqueous NaOH. After filtration, the product was isolated in 78% yield. Alternatively, the product has been isolated by chromatography in 83% yield. MS (Turbo Spray): 207 (52%), 205 (M+H+, 100%), 170 (9%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150594B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-7edb18f42afa4141af164c1b02067dfe |
| Source note | uspto-grants-2015_10 |