HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 522990Generated: October 29, 2026
Cesium carbonate → N-tert-butyl-2-(6-(methylsulfonyl)pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide
https://huagongshe.com/reaction/522990
Participants
| Role | Name | HCID | Charge |
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| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 6-(Methanesulfonyl)pyridin-3-amine | HCID 20038977 | — |
| Reactant | 2-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide | HCID 71575645 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-tert-butyl-2-(6-(methylsulfonyl)pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide | HCID 90041549 | 53.3% |
Reaction Steps
A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (150 mg, 351 μmol), 6-(methylsulfonyl)pyridin-3-amine (90.7 mg, 526 μmol), xantphos (60.9 mg, 105 μmol), Pd2(dba)3 (32.1 mg, 35.1 μmol) and cesium carbonate (229 mg, 702 μmol) in dioxane (2.4 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled then filtered through a pad of celite. The filtrate was concentrated in vacuo then purified by chromatography (silica, 20-95% ethyl acetate in hexanes) to give N-tert-butyl-2-(6-(methylsulfonyl)pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (97 mg, 187 μmol, 53%) as a yellow solid. (EI/CI) m/z: 458.3 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09334278B2 |
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| Source dataset | uspto-grants-2016_05 |
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| ORD ID | ord-868ed8b26f39466e9e78c9fc16a32770 |
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| Source note | uspto-grants-2016_05 |
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