HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-amino-N-(pyridin-3-ylmethyl)benzamide → 4-(5-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-amino-N-(pyridin-3-ylmethyl)benzamide | HCID 577833 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 8-Bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine | HCID 57664373 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-(5-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide | HCID 57664352 | 71.8% |
Reaction Steps
A solution of 8-bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine (100 mg, 0.43 mmol), 4-Amino-N-pyridin-3-ylmethyl-benzamide (108 mg, 0.48 mmol), sodium-tert-butoxide (58 mg, 0.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (39 mg, 40 μmol) and Xantphos (50 mg, 90 μmol) in dioxane is degassed for one minute by nitrogen bubbling and then irradiated in a sealed tube in a microwave (CEM Explorer) under a nitrogen atmosphere for 30 minutes at 110° C. The solvent is evaporated and the crude is dissolved in dichloromethane and filtered in order to remove the palladium catalyst. The residue is purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 95:5) affording the title compound (117 mg) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07977352B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-59b662cc73ee4a0c8764bd687c820646 |
| Source note | uspto-grants-2011_07 |