Methyl 3-(bromomethyl)benzoate → 3-[2-(4-Chloro-2-methoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-benzoic acid methyl ester

HRID 1875801Notes

Reaction equation

HRID 1875801 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(CC3CCCCC3)C3C=C(F)C(F)=CC=3N=2)=C(OCC2C=CC=CC=2Cl)C=1.[CH3:72][O:73][C:74](=[O:83])[C:75]1[CH:80]=[CH:79][CH:78]=[C:77]([CH2:81]Br)[CH:76]=1>>[CH3:72][O:73][C:74](=[O:83])[C:75]1[CH:80]=[CH:79][CH:78]=[C:77]([CH2:81][N:12]2[C:11]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:10]=3[N:9]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[O:31][CH3:32])[CH:76]=1

Participants

4

Reactant 3

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 582092583-{4-[2-(4-Chloro-2-cyclopentylmethoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-phenyl}-propionic acidHCID 582092722-[4-Chloro-2-(2-chloro-benzyloxy)-phenyl]-1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 670501023-[2-(4-Chloro-2-methoxy-phenyl)-5,6-difluoro-benzoimidazol-1-ylmethyl]-benzoic acid methyl ester

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 (3-bromomethyl-benzoic acid methyl ester CAS Reg. No. 1129-28-8). Brown sticky solid (67%). MS (Turbo Spray): m/z=443.2 (M+H).

Sources & evidence

ORD record
ord-915478001b70427dba62954d03ecb802
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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