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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204317Generated: November 2, 2026

3-Chloro-4-fluoroaniline → 2-Bromo-5-[5-chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-yl]-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

https://huagongshe.com/reaction/2204317

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Chloro-4-fluoroanilineHCID 9708—
Reactant5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl esterHCID 86703101—
Reactant2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl esterHCID 86703105—
Reactant5-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-oneHCID 86703124—
Product2-Bromo-5-[5-chloro-1-(4-methoxy-benzyl)-6-oxo-1,6-dihydro-pyridin-3-yl]-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-oneHCID 86703123—

Reaction Steps

The title compound was prepared in analogy to the procedure described for Step D2, but 2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester (Step E4) and 5-amino-3-chloro-1-(4-methoxy-benzyl)-1H-pyridin-2-one (Step O4) were used instead of 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester and 3-chloro-4-fluoroaniline respectively to afford the title compound as a green-blue foam. tR: 5.47 min (HPLC 1); ESI-MS: tR=1.33 min, [M+H]+ 568/570/572 (LC-MS 1); TLC: Rf=0.30 (1:1 EtOAc/heptanes).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365576B2
Source datasetuspto-grants-2016_06
ORD IDord-c99e317e2cba4a9091afce2f133fd4c2
Source noteuspto-grants-2016_06