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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1056792Generated: October 30, 2026

Cesium carbonate → 6-Chloro-2-(3-oxo-cyclopent-1-enyl)-quinoline-5-carboxylic acid (1-hydroxy-3-methylcyclo hexyl methyl)-amide

https://huagongshe.com/reaction/1056792

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclopenten-1-oneHCID 66822876—
Reactant2,6-Dichloro-quinoline-5-carboxylic acid (1-hydroxy-3methyl-cyclohexylmethyl)-amideHCID 86623365—
CatalystHCID 178477754HCID 178477754—
Product6-Chloro-2-(3-oxo-cyclopent-1-enyl)-quinoline-5-carboxylic acid (1-hydroxy-3-methylcyclo hexyl methyl)-amideHCID 118566707—

Reaction Steps

The title compound was synthesized according to the procedure described in example 125 using 2,6-dichloro-quinoline-5-carboxylic acid (1-hydroxy-3-methyl-cyclohexylmethyl)-amide, cesium carbonate, 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-cyclopent-2-enone and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II). 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.70 (t, J=6.04 Hz, 1H), 8.28-8.22 (m, 2H), 8.12 (d, J=9.21 Hz, 1H), 7.86 (d, J=9.03 Hz, 1H), 7.13 (t, J=1.64 Hz, 1H), 4.21 (s, 1H), 3.22-3.20 (m, 2H), 2.56-2.54 (m, 2H), 1.73 (t, J=3.41 Hz, 1H), 1.62-1.56 (m, 4H), 1.48-1.45 (m, 1H), 1.32-1.25 (m, 1H), 1.06-1.00 (m, 1H), 0.84 (d, J=6.63 Hz, 3H), 0.77-0.74 (m, 1H). m/z: 413.2 [M+H]+

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09399623B2
Source datasetuspto-grants-2016_07
ORD IDord-91cccf9e4fa646a0ac16af659511bcce
Source noteuspto-grants-2016_07