HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 251022Generated: October 26, 2026
Indole → 3-Indol-1-yl-pyridine-2-carbonitrile
https://huagongshe.com/reaction/251022
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Indole | HCID 798 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Bromopyridine-2-carbonitrile | HCID 817694 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 3-Indol-1-yl-pyridine-2-carbonitrile | HCID 67271706 | 89% |
Reaction Steps
To a solution of 3-bromo-2-cyanopyridine (Sakamoto, T. et al., Chem. Pharm. Bull. 1985, 33(2), 565-571) (340 mg, 1.86 mmol) and indole (436 mg, 3.72 mmol) in toluene (15 mL) was added Cs2CO3 (737 mg, 2.26 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (83 mg, 0.143 mmol) and Pd2(dba)3 (42 mg, 0.046 mmol) and the reaction stirred at 110° C. for 2.5 d. The mixture was concentrated and purified by column chromatography on silica gel (EtOAc/Hexanes, 2:1) to give 3-indol-1-yl-pyridine-2-carbonitrile (362 mg, 89%) as a beige solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07863293B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-c75c30a8e3a5439193376c99a7645a8a |
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| Source note | uspto-grants-2011_01 |
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