3-Chloro-4-fluoroaniline → 2-Bromo-5-[(3-chloro-4-fluoro-phenyl)-4-chloro-phenylamino]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

HRID 2410103Notes

Reaction equation

HRID 2410103 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:22])[CH3:21])[C:10]=1C(C1C=CC(Cl)=CC=1)O)=[O:5])[CH3:2].[Cl:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][C:31]=1[F:32])[NH2:28]>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([Br:23])[N:9]([CH:20]([CH3:21])[CH3:22])[C:10]=1[N:28]([C:27]1[CH:29]=[CH:30][C:31]([F:32])=[C:25]([Cl:24])[CH:26]=1)[C:29]1[CH:27]=[CH:26][C:25]([Cl:24])=[CH:31][CH:30]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 86707749ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylate2×

Product 1

HCID 867077602-Bromo-5-[(3-chloro-4-fluoro-phenyl)-4-chloro-phenylamino]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester

Procedure

The title compound was prepared in analogy to the procedure described for step E2 using 2-bromo-5-[(4-chlorophenyl)-hydroxy-methyl]-1-isopropyl-1H-imidazole-4-carboxylic acid ethyl ester (intermediate B) and 3-chloro-4-fluoro-aniline as starting materials. tR 1.38 min (LC-MS 2); ESI-MS: 530.1 [M+H]+ (LC-MS 2).

Sources & evidence

ORD record
ord-e5a8c247190d48b29ebaaa2ca620e630
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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