HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 535399Generated: October 31, 2026
Sodium Carbonate → tert-butyl-N-[1-[[5-(3,5-dimethylpyridin-4-yl)-6-[2-tri(propan-2-yl)silylethynyl]pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate
https://huagongshe.com/reaction/535399
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 3,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 45588136 | — |
| Reactant | Tert-butyl (1-((5-bromo-6-((triisopropylsilyl)ethynyl)pyridin-2-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate | HCID 86694383 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Solvent | Water | HCID 962 | — |
| Product | tert-butyl-N-[1-[[5-(3,5-dimethylpyridin-4-yl)-6-[2-tri(propan-2-yl)silylethynyl]pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate | HCID 86694382 | — |
Reaction Steps
A mixture of tert-butyl-N-[1-[[5-bromo-6-[2-tri(propan-2-yl)silylethynyl]pyridin-2-yl]-amino]-1-oxopropan-2-yl]-N-methylcarbamate C1a (300 mg, 0.56 mmol), 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (169 mg, 0.72 mmol), Na2CO3 (118 mg, 1.11 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (40.8 mg, 0.06 mmol), dioxane (2 ml) and water (0.4 ml) is stirred under argon atmosphere for 17 h at 90° C. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 26 mg (51%). HPLC-MS: M+H=565; tR=2.32 min (*Method—4).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08859541B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-f98524c63a444f8e8fb942356918e410 |
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| Source note | uspto-grants-2014_10 |
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