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

HRID 1875817Notes

Reaction equation

HRID 1875817 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](CC3C=CC(CCC(O)=O)=CC=3)[C:11]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:10]=3[N:9]=2)=[C:4]([O:31][CH2:32]C2CCCC2)[CH:3]=1.ClC1C=CC(C2N(CC3C=C(C=CC=3)C(O)=O)C3C=C(F)C(F)=CC=3N=2)=C(OCC2CCCC2)C=1.Br[CH2:74][C:75]1[CH:82]=[CH:81][C:78]([C:79]#[N:80])=[CH:77][C:76]=1[F:83]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:74][C:75]3[CH:82]=[CH:81][C:78]([C:79]#[N:80])=[CH:77][C:76]=3[F:83])[C:11]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:10]=3[N:9]=2)=[C:4]([O:31][CH3:32])[CH:3]=1

Participants

4

Reactant 3

HCID 27831494-(Bromomethyl)-3-fluorobenzonitrileHCID 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 670499704-[2-(4-Chloro-2-methoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-3-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-3-fluoro-benzonitrile (CAS Reg. No. 105942-09-4). Brown sticky solid (31%). MS (Turbo Spray): m/z=428.2 (M+H).

Sources & evidence

ORD record
ord-6cf50876043c438c9e73aba8d7e8537f
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

Loading…