HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2075682Generated: October 30, 2026
Diisopropylethylamine → 4-[3-Fluoro-5-(1-methyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile
https://huagongshe.com/reaction/2075682
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-Fluoro-5-mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile | HCID 11356823 | — |
| Reactant | 7-Bromo-1-methyl-imidazo[1,5-a]quinoline | HCID 67091375 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-[3-Fluoro-5-(1-methyl-imidazo[1,5-a]quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile | HCID 67090859 | — |
Reaction Steps
4d (80 mg, 0.3 mmol) and 4-(3-Fluoro-5-mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (4e, 88 mg, 0.37 mmol) were dissolved in 1,4-dioxane (3 mL) and degassed for 10 minutes with N2. iPr2NEt (0.10 mL, 0.6 mmol), Pd2dba3 (14 mg, 0.02 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (17 mg, 0.03 mmol) were added, and the reaction was degassed for another 10 minutes with N2. The reaction was then sealed and heated to 80° C. overnight. After cooling to room temperature, the reaction was concentrated and purified by silica gel chromatography (0-20% MeOH in EtOAc) to give the desired product, 4f.
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-ba83cd971ad74d1991c51dbf3852ab30 |
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| Source note | uspto-grants-2011_04 |
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