Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Azetidine | HCID 10422 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Phenolate Sodium | HCID 4445035 | — |
| Reactant | HCID 123587010 | HCID 123587010 | — |
| Catalyst | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 123897862 | HCID 123897862 | 15.4% |
Reaction Steps
A solution of 2-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (28 mg, 83.8 μmol, Eq: 1.00) in dioxane (1 ml) was purged with argon, then sodium phenoxide (14.6 mg, 126 μmol, Eq: 1.5), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xant-phos) (3.88 mg, 6.7 μmol, Eq: 0.08), tris(dibenzylideneacetone)dipalladium chloroform complex/Pd2(dba)3CHCl3 (3.47 mg, 3.35 μmol, Eq: 0.04) and azetidine (9.57 mg, 11.3 μl, 168 μmol, Eq: 2) were added. The vial was capped and irradiated at 140° C. for 30 minutes in the microwave oven. The crude material was applied on silicagel and purified by chromatography over a 5 g silicagel column using ethyl acetate/methanol 0-10% as eluent affording 2-[2-(5-azetidin-1-yl-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (4 mg/15.4%) as a light yellow solid. MS: m/e=311.4 (M+H+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09394311B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-d106a6ce17f24035810edb9c2cd512b0 |
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| Source note | uspto-grants-2016_07 |
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