HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 522984Generated: October 29, 2026
Cesium carbonate → HCID 90041581, compound
https://huagongshe.com/reaction/522984
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-(Methylsulfonyl)aniline | HCID 79617 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 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 | HCID 90041581 | HCID 90041581 | 59.6% |
Reaction Steps
A mixture of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 292 μmol), 4-(methylsulfonyl)aniline (75.1 mg, 439 μmol), xantphos (50.8 mg, 87.7 μmol), Pd2(dba)3 (26.8 mg, 29.2 μmol) and cesium carbonate (191 mg, 585 μmol) in dioxane (2 mL) was heated in a microwave at 150° C. for 20 min. The mixture was cooled, filtered through celite, and the filtrate concentrated in vacuo. Purification by chromatography (silica, 20-75% ethyl acetate in hexanes) gave N-tert-butyl-2-(4-(methylsulfonyl)phenylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (90 mg, 174 μmol, 59%) as a light yellow solid. (EI/CI) m/z: 518.3 [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-2b1491e0dc6543a0b70d79b083320af3 |
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| Source note | uspto-grants-2016_05 |
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