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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204351Generated: October 31, 2026

3-Chloro-4-fluoroaniline → 2-Bromo-6-(4-chloro-2-fluoro-phenyl)-5-(2,5-dimethyl-2H-pyrazol-3-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

https://huagongshe.com/reaction/2204351

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Chloro-4-fluoroanilineHCID 9708—
ReactantMethanesulfonic anhydrideHCID 81560—
Reactant1,3-Dimethyl-1H-pyrazol-5-amineHCID 520721—
Reactant5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl esterHCID 86703101—
Reactant5-bromo-2-[(4-chloro-2-fluoro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl esterHCID 86703158—
SolventTriethylamineHCID 8471—
Product2-Bromo-6-(4-chloro-2-fluoro-phenyl)-5-(2,5-dimethyl-2H-pyrazol-3-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-oneHCID 86703157—

Reaction Steps

The title compound was prepared in analogy to the procedure described for Intermediate D but in the step corresponding to Step D2, 2,5-dimethyl-2H-pyrazol-3-ylamine [3524-32-1] and 5-bromo-2-[(4-chloro-2-fluoro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step BI1) were used instead of 3-chloro-4-fluoroaniline and 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester respectively. Moreover, in this step, the procedure described for Step L3 using Ms2O and Et3N was used. The title compound (containing some of the corresponding 2-chloro analog) was obtained as a solid. ESI-MS: tR=1.14 min, [M+H]+ 465/467/469 (LC-MS 1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365576B2
Source datasetuspto-grants-2016_06
ORD IDord-8455e3d55da34de0a0633a68dfb4c05d
Source noteuspto-grants-2016_06