4-Cyano-3-fluorobenzyl bromide → 4-[2-(4-Chloro-2-methoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-2-fluoro-benzonitrile

HRID 1875815Notes

Reaction equation

HRID 1875815 reaction equation
ClC1C=CC(C2N(CC3C=CC(CCC(O)=O)=CC=3)C3C=C(F)C(F)=CC=3N=2)=C(OCC2CCCC2)C=1.[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[N:49](CC3C=C(C=CC=3)C(O)=O)[C:48]3[CH:60]=[C:61]([F:65])[C:62]([F:64])=[CH:63][C:47]=3[N:46]=2)=[C:41]([O:66][CH2:67]C2CCCC2)[CH:40]=1.Br[CH2:74][C:75]1[CH:82]=[CH:81][C:78]([C:79]#[N:80])=[C:77]([F:83])[CH:76]=1>>[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[N:49]([CH2:74][C:75]3[CH:82]=[CH:81][C:78]([C:79]#[N:80])=[C:77]([F:83])[CH:76]=3)[C:48]3[CH:60]=[C:61]([F:65])[C:62]([F:64])=[CH:63][C:47]=3[N:46]=2)=[C:41]([O:66][CH3:67])[CH:40]=1

Participants

4

Reactant 3

HCID 27784664-Cyano-3-fluorobenzyl bromideHCID 582092583-{4-[2-(4-Chloro-2-cyclopentylmethoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-phenyl}-propionic acidHCID 582092763-[2-(4-Chloro-2-cyclopentylmethoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-benzoic acid2×

Product 1

HCID 670498704-[2-(4-Chloro-2-methoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-2-fluoro-benzonitrile

Procedure

The title compound was prepared in analogy to Example 19, intermediate b, from 2-(4-chloro-2-methoxy-phenyl)-5,6-difluoro-1H-benzoimidazole (Example 19, intermediate c) and 4-bromomethyl-2-fluoro-benzonitrile (CAS Reg. No. 222978-03-2). Brown sticky solid (39%). MS (Turbo Spray): m/z=428.2 (M+H).

Sources & evidence

ORD record
ord-30e03cf9e58146dca1ddb6cb8367535f
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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