HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 624851Generated: October 25, 2026
Cesium carbonate → 5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridine-2-carbonitrile
https://huagongshe.com/reaction/624851
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (4-Fluorobenzyl)boronic acid | HCID 45090593 | — |
| Reactant | 6-Bromomethyl-5-cyclopropyl-pyridine-2-carbonitrile | HCID 86674770 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-Cyclopropyl-6-(4-fluoro-benzyl)-pyridine-2-carbonitrile | HCID 71087459 | 79.3% |
Reaction Steps
A mixture of 6-bromomethyl-5-cyclopropyl-pyridine-2-carbonitrile (0.1 g, 0.4 mmol), 4-fluoro-benzylboronic acid (CAN 1765-93-1, 0.1 g, 0.7 mmol), Pd(dppf)Cl2 (CAN 95464-05-4, 50 mg, 0.068 mmol), Cs2CO3 (0.2 g, 0.6 mmol) in 1.4-dioxane (10 mL) was stirred for 12 h at 110° C. under a nitrogen atmosphere. The mixture was filtered, concentrated and purified by flash column chromatography (silica gel, 3 g, eluting with 25% ethyl acetate in petroleum ether) to give the title compound (80 mg, 75%) as yellow solid; MS (EI): m/e=253.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09303012B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-8df06f2758b844d596d5e8edc5fab8ca |
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| Source note | uspto-grants-2016_04 |
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