HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2075669Generated: October 31, 2026
Nitrogen → 4-[3-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid methyl ester
https://huagongshe.com/reaction/2075669
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | 3-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-propionic acid 2-ethyl-hexyl ester | HCID 67090999 | — |
| Reactant | Methyl 4-(3-bromophenyl)tetrahydro-2H-pyran-4-carboxylate | HCID 67091038 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-[3-(5-Phenyl-imidazo[1,2-a]quinolin-8-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carboxylic acid methyl ester | HCID 24875866 | — |
Reaction Steps
1x (200 mg, 0.43 mmol) in 1,4-dioxane (5 mL) was degassed with N2 for 10 minutes and cooled to 0° C. Potassium tert-butoxide (73 mg, 0.65 mmol) was added, and the mixture was stirred at room temperature for 5 minutes. The solution was degassed with N2 for another 5 minutes while 4-(3-bromo-phenyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (1y, 130 mg, 0.43 mmol), Pd2dba3 (10 mg, 0.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (11 mg, 0.02 mmol), and iPr2NEt (0.15 mL, 0.87 mmol) were added. The reaction was heated to 60° C. overnight, and then cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the desired product, 1z.
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-4468fc6ac7294dda8247df2651c363dc |
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| Source note | uspto-grants-2011_04 |
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