Diethyl aluminum chloride → 2-Bromo-5-(3-chloro-4-fluoro-phenyl)-6-(5-chloro-pyridin-2-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204352Notes

Reaction equation

[Cl-].C([Al+]CC)C.C[O:8][C:9]([C:11]1[CH:15]=[C:14]([Br:16])[N:13]([CH:17]([CH3:19])[CH3:18])[C:12]=1[CH:20]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[C:31]([Cl:36])[CH:30]=1)[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=1)=O>>[Br:16][C:14]1[N:13]([CH:17]([CH3:18])[CH3:19])[C:12]2[CH:20]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=3)[N:28]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[C:31]([Cl:36])[CH:30]=3)[C:9](=[O:8])[C:11]=2[CH:15]=1

Participants

Reactant 2

HCID 16686102Diethyl aluminum chloride

HCID 867031605-bromo-2-[(3-chloro-4-fluoro-phenylamino)-(5-chloro-pyridin-2-yl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 867031592-Bromo-5-(3-chloro-4-fluoro-phenyl)-6-(5-chloro-pyridin-2-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Procedure

The title compound was prepared in analogy to the procedure described for Step H1, but diethylaluminium chloride (1.8M in toluene) was used instead of trimethylaluminium chloride, and 5-bromo-2-[(3-chloro-4-fluoro-phenylamino)-(5-chloro-pyridin-2-yl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step BL1) was used instead of 2-[(3-chloro-4-fluoro-phenylamino)-(4-cyano-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester to afford the title compound as a yellow solid. ESI-MS: tR=1.30 min, [M+H]+ 482/484/486 (LC-MS 1).

Workup

customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record: ord-4c6e3f282b3547f5ac587f0f95a4b341
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365576B2

Reaction notes

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