HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine → N2-[(3,4-Dimethoxyphenyl)methyl]-6-(trifluoromethyl)[4,4′-bipyridine]-2,3′-diamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine | HCID 49760414 | — |
| Reactant | N-(3,4-dimethoxybenzyl)-4-iodo-6-(trifluoromethyl)pyridin-2-amine | HCID 69047366 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | N2-[(3,4-Dimethoxyphenyl)methyl]-6-(trifluoromethyl)[4,4′-bipyridine]-2,3′-diamine | HCID 68161531 | 38% |
Reaction Steps
Method 26 was followed using N-(3,4-dimethoxybenzyl)-4-iodo-6-(tri-fluoromethyl)pyridin-2-amine (1.0 equiv.), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (3 equiv.), Pd(dppf)Cl2 DCM (0.10 equiv.) in DME/2M Na2CO3 (3:1, 0.07 M) at 50° C. for 45 min. Purification via reverse phase HPLC afforded N2-(3,4-dimethoxybenzyl)-6-(trifluoromethyl)-4,4′-bipyridine-2,3′-diamine in 38% yield. LCMS (m/z): 402.1 (MH+); LC Rt=3.0 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822497B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-91938574c3d44959a778d2be9cb33081 |
| Source note | uspto-grants-2014_09 |