HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Benzyloxy-phenylboronic acid → 6-{2-[6-(3-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Benzyloxy-phenylboronic acid | HCID 2734313 | — |
| Reactant | HCID 178428704 | HCID 178428704 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 6-{2-[6-(3-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine | HCID 178428710 | 61% |
Reaction Steps
The title compound is synthesized according to General Procedure A. 150 mg of 2-[2-(2-amino4-methylpyridin-6-yl)ethyl]-6-bromo-3H-imidazo[4,5-b]pyridine in 7.5 ml dioxane, 1.36 ml Na2CO3 solution, 116 mg of 3-benzyloxyphenylboronic acid, 20 mg of PdCl2(PCy3)2, 120° C. for 48 h, 20 ml of CH2Cl2/H2O, 220 mg of crude title compound is purified by re-crystallization from 6.0 ml isopropyl alcohol to yield 120 mg of the title compound. M.p. 181° C. ESI-MS: 436.3 (MH+). TLC: Rf=0.30 (dichloromethane/methanol 10:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07781453B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-65aa673bc9ab4b87bc90ccbc045fc620 |
| Source note | uspto-grants-2010_08 |