Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Bromopyridine | HCID 12286 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 86607567 | HCID 86607567 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 11688679 | HCID 11688679 | 41% |
Reaction Steps
In a 5 ml microwave reaction vessel were dissolved 80 mg (0.31 mmol) 3-Amino-6-methyl-pyridine-2-carboxylic acid (2-chloro-pyridin-4-yl)-amide and 60 mg (0.38 mmol, 1.25 equiv.) of 3-Bromopyridine in 4 ml of dioxane. Cesium carbonate (139 mg, 0.43 mmol, 1.4 equiv.) were added and argon was bubbled through the suspension for 3 min. Then Xanthphos (58 mg, 0.10 mmol, 0.33 equiv.) and Pd2(dba)3.CHCl3 (32 mg, 0.03 mmol, 0.1 equiv.) were added and the mixture was heated for 2 h at 160° C. under microwave irradiation. To the mixture was added silica gel (5 g) and the mixture was evaporated to dryness in vaccuo. The powder was charged onto a flash chromatography column and eluted (heptane/ethyl acetate 2:1) to yield the title compound as a yellow solid (total 43 mg, 41%), MS (ISP): m/e=340.1, 342.0 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07414060B2 |
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| Source dataset | uspto-grants-2008_08 |
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| ORD ID | ord-7672228fa90744a78b45afa69ab3fd08 |
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| Source note | uspto-grants-2008_08 |
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