Diethyl aluminum chloride → 2-Bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrole-3-carboxylic acid ethyl ester
Reaction equation
[Cl-].C([Al+]CC)C.[CH2:7]([O:9][C:10]([C:12]1[C:16]([C:17](OCC)=[O:18])=[C:15]([CH:22]([NH:30][C:31]2[CH:36]=[C:35]([Cl:37])[C:34](=[O:38])[N:33]([CH3:39])[CH:32]=2)[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[N:14]([CH:40]([CH3:42])[CH3:41])[C:13]=1[Br:43])=[O:11])[CH3:8]>>[CH2:7]([O:9][C:10]([C:12]1[C:16]2[C:17](=[O:18])[N:30]([C:31]3[CH:36]=[C:35]([Cl:37])[C:34](=[O:38])[N:33]([CH3:39])[CH:32]=3)[CH:22]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[C:15]=2[N:14]([CH:40]([CH3:42])[CH3:41])[C:13]=1[Br:43])=[O:11])[CH3:8]Participants
3
Reactant 2
Product 1
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 2-bromo-5-[(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-ylamino)-(4-chloro-phenyl)-methyl]-1-isopropyl-1H-pyrrole-3,4-dicarboxylic acid diethyl ester (Step BM1) 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 beige solid. tR: 1.16 min (HPLC 3); ESI-MS: tR=1.11 min, [M+H]+ 566/568/570 (LC-MS 1); TLC: Rf=0.14 (EtOAc).
Workup
- customThe title compound was prepared in analogy to the procedure
Sources & evidence
- ORD record
- ord-f8d5680769ed479dbaafffbf7214b091
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365576B2
Reaction notes
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