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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1929221Generated: November 2, 2026

Diisopropylethylamine → 4-Isobutoxy-1h-indole-2-carboxylic acid {1-[2-(3-fluoro-piperidin-1-yl)-ethyl]-piperidin-4-yl}-amide

https://huagongshe.com/reaction/1929221

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant3-FLUOROPIPERIDINE HYDROCHLORIDEHCID 2759156—
Reactant4-Isobutoxy-1h-indole-2-carboxylic acid {1-[2-(3,6-dihydro-2h-pyridin-1-yl)-ethyl]-piperidin-4-yl}-amideHCID 58916326—
ReactantCyanomethyl-triphenyl phosphonium iodideHCID 87175442—
SolventPropionitrileHCID 7854—
SolventEthyl AcetateHCID 8857—
Product4-Isobutoxy-1h-indole-2-carboxylic acid {1-[2-(3-fluoro-piperidin-1-yl)-ethyl]-piperidin-4-yl}-amideHCID 59600197—

Reaction Conditions

Temperature90 °C

Reaction Steps

To a suspension of 190 (see example 150) (100 mg, 0.28 mmol), 3-fluoropiperidine hydrochloride (43 mg, 0.208 mmol) and DIEA (0.189 ml, 1.12 mmol) in 0.5 ml of propionitrile is added cyanomethyl-triphenyl phosphonium iodide (81 mg, 0.336 mmol). The mixture is heated at 90° C. for 14 hours. The resulting solution is then diluted with EtOAc (20 ml) and washed twice with saturated sodium bicarbonate, dried over sodium sulfate and evaporated. The crude product is further purified by preparative HPLC.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08183366B2
Source datasetuspto-grants-2012_05
ORD IDord-65dcf333f78c4dd0b08b47696bc29889
Source noteuspto-grants-2012_05