HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 927588Generated: October 31, 2026
Cesium carbonate → 5-Cyclopropyl-6-methyl-pyridine-2-carbonitrile
https://huagongshe.com/reaction/927588
Participants
| Role | Name | HCID | Charge |
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| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | 5-Bromo-6-methylpyridine-2-carbonitrile | HCID 49818779 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-Cyclopropyl-6-methyl-pyridine-2-carbonitrile | HCID 86674769 | 75.9% |
Reaction Steps
5-Bromo-6-methyl-pyridine-2-carbonitrile (0.5 g, 2.5 mmol), cyclopropylboronic acid (CAN:411235-57-9, 0.36 g, 4 mmol), Pd2(dba)3 (CAN:411235-57-9, 0.1 g, 0.2 mmol), xantphos (CAN:161265-03-8, 0.15 g, 0.26 mmol) and Cs2CO3 (1.1 g, 3 mmol) were suspended in 1,4-dioxane (30 mL) under a nitrogen atmosphere. The mixture was stirred for 12 h at 110° C., filtered, concentrated under reduced pressure and purified by column chromatography (silica gel, 5 g, eluting with 10% ethyl acetate in petroleum ether) to give the title compound (0.3 g, 75%) as yellow solid; MS (D): m/e=159.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09290451B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-3e8769d2bda94999afbb5997f9db0274 |
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| Source note | uspto-grants-2016_03 |
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