HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2075661Generated: November 2, 2026
Diisopropylethylamine → 4-[3-(2,4-Dichloro-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile
https://huagongshe.com/reaction/2075661
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 4-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile | HCID 18786386 | — |
| Reactant | 2,4-Dichloro-7-iodo-quinoline | HCID 86613821 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-[3-(2,4-Dichloro-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile | HCID 86613825 | — |
Reaction Steps
2,4-Dichloro-7-iodo-quinoline (1.7 g, 5.26 mmol) and 4-(3-mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (1p, 1.27 g, 5.79 mmol) were dissolved in 1,4-dioxane (50 mL) and degassed with N2 for 10 minutes. Pd2dba3 (120 mg, 0.13 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (150 mg, 0.27 mmol) were added, followed by iPr2NEt (1.4 mL, 7.9 mmol), and the reaction was heated to 70° C. for 2 hours. The mixture was diluted with EtOAc and water, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the desired product, 1q.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07919621B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-40be5a30271d4292b5c100ae1d831d76 |
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| Source note | uspto-grants-2011_04 |
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