HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 523002Generated: October 26, 2026
Cesium carbonate → HCID 90041605, compound
https://huagongshe.com/reaction/523002
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 3-Bromo-5-(methylsulfonyl)pyridine | HCID 22391981 | — |
| Reactant | HCID 90041356 | HCID 90041356 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90041605 | HCID 90041605 | 95.3% |
Reaction Steps
To a mixture of 2-amino-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (92 mg, 253 mol), 3-bromo-5-(methylsulfonyl)pyridine (77.7 mg, 329 mol), xantphos (43.9 mg, 75.9 mol), Pd2(dba)3 (23.2 mg, 25.3 mol) and cesium carbonate (165 mg, 506 mol) in dioxane (2 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, 30-70% ethyl acetate in hexanes) to give N-tert-butyl-2-(5-(methylsulfonyl)pyridin-3-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (125 mg, 241 mol, 95%) as a yellow gum. (EI/CI) m/z: 519.3 [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-ac371b25a4a3452aaf94fa2389b61fdf |
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| Source note | uspto-grants-2016_05 |
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