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

HRID 2410098Notes

Reaction equation

HRID 2410098 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].[F:24][C:25]1[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27]>>[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:27]([C:26]1[CH:28]=[CH:29][CH:30]=[C:31]([Cl:32])[C:25]=1[F:24])[C:28]1[CH:26]=[CH:25][C:31]([Cl:32])=[CH:30][CH:29]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 750143-Chloro-2-fluoroanilineHCID 86707749ethyl 2-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-isopropyl-1H-imidazole-4-carboxylate2×

Product 1

HCID 867077552-Bromo-5-[(3-chloro-2-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 2-fluoro-3-chloro-aniline as starting materials; 1H-NMR (DMSO-d6, 400 MHz) δ ppm 7.46 (d, 2H), 7.30 (d, 2H), 6.98 (dd, 1H), 6.82 (d, 1H), 6.73-6.69 (m, 2H), 4.82 (sep (1H), 4.26 (q, 2H), 1.45 (d, 3H), 1.24 (t, 3H), 1.17 (d, 3H).

Sources & evidence

ORD record
ord-ff18e839ba924bbbbed015ce3dbf7124
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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