HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1022049Generated: October 29, 2026
Potassium Acetate → 3-(Acetoxymethyl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)pyridin-4-ylboronic Acid
https://huagongshe.com/reaction/1022049
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reactant | (4-Chloro-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)pyridin-3-yl)methyl acetate | HCID 86684463 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3-(Acetoxymethyl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-2(1H)-yl)pyridin-4-ylboronic Acid | HCID 86684464 | 108.7% |
Reaction Steps
A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 244b (900 mg, 2.4 mmol), Pin2B2 (3.05 g, 12 mmol), Pd(dppf)Cl2 (98 mg, 0.12 mmol), X-phos (114 mg, 0.24 mmol), potassium acetate (720 mg, 7.2 mmol), and dioxane (20 mL). After three cycles of vacuum/argon flush, the mixture was heated at 65° C. for 4 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was washed with 5:1 petroleum ether/ethyl acetate (10 mL) to afford 244c as a yellow solid (1.0 g, purity: 60%). MS-ESI: [M+H]+ 384.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08716274B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-db8bc880a90e4cd7854de792f8b47e6f |
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| Source note | uspto-grants-2014_05 |
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