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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1839836Generated: October 27, 2026

1,2-Dichloroethane → 4-(3-Fluoro phenyl)-3-[1-{3-[(r)-2-((s)-3-fluoro-pyrrolidin-1-ylmethyl)-pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

https://huagongshe.com/reaction/1839836

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DichloroethaneHCID 11—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant2-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z) ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acidHCID 69740587—
SolventDimethylformamideHCID 6228—
SolventDichloromethaneHCID 6344—
Product4-(3-Fluoro phenyl)-3-[1-{3-[(r)-2-((s)-3-fluoro-pyrrolidin-1-ylmethyl)-pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-oneHCID 60061579—

Reaction Steps

To a solution of 2-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-5-methyl-1H-pyrrole-3-carboxylic acid (100 mg, 0.28 mmol), EDC (120 mg, 0.63 mmol), HOBt (40 mg, 0.3 mmol) in DMF (4 mL) was added TEA (0.15 mL) and (S)-3-fluoro-1-(R)-1-pyrrolidin-2-ylmethyl-pyrrolidine (95 mg, 0.55 mmol). The mixture was stirred at rt for 20 hours. The reaction was diluted with DCM, washed with water, NaHCO3, dried and concentrated. The residue was purified on a silica gel column to give the titled compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06677368B2
Source datasetuspto-grants-2004_01
ORD IDord-0d0a727f2c6842cda9ca159c3c52d613
Source noteuspto-grants-2004_01