Diethyl aluminum chloride → 2-Bromo-5-(3-chloro-2-fluorophenyl)-6-(5-chloropyridin-2-yl)-1-isopropyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one

HRID 2204357Notes

Reaction equation

HRID 2204357 reaction equation
[Cl-].C([Al+]CC)C.[Br:7][C:8]1[N:12]([CH:13]([CH3:15])[CH3:14])[C:11]([CH:16]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=2[F:32])[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)=[C:10]([C:33]([O:35]C)=O)[CH:9]=1>>[Br:7][C:8]1[N:12]([CH:13]([CH3:14])[CH3:15])[C:11]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=3)[N:24]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=3[F:32])[C:33](=[O:35])[C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 16686102Diethyl aluminum chlorideHCID 86703167methyl 5-bromo-2-(((3-chloro-2-fluorophenyl)amino)(5-chloropyridin-2-yl)methyl)-1-isopropyl-1H-pyrrole-3-carboxylate

Product 1

HCID 867031662-Bromo-5-(3-chloro-2-fluorophenyl)-6-(5-chloropyridin-2-yl)-1-isopropyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-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 methyl 5-bromo-2-(((3-chloro-2-fluorophenyl)amino)(5-chloropyridin-2-yl)methyl)-1-isopropyl-1H-pyrrole-3-carboxylate (Step BT1) 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 green solid. ESI-MS: tR=1.27 min, [M+H]+ 482/484/486 (LC-MS 1).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-7d19a3c3916f480d878fb08a27146d23
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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