Methyl 4-(bromomethyl)-3-fluorobenzoate → 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxymethyl}-3-fluoro-benzoic methyl ester

HRID 417103Notes

Reaction equation

HRID 417103 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:14][O:15]CC3CCCCC3)[C:11]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH3:35][O:36][C:37](=[O:47])[C:38]1[CH:43]=[CH:42][C:41]([CH2:44]Br)=[C:40]([F:46])[CH:39]=1>>[CH3:35][O:36][C:37](=[O:47])[C:38]1[CH:43]=[CH:42][C:41]([CH2:44][O:15][CH2:14][CH:13]([N:12]2[C:11]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=3[N:9]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:40]([F:46])[CH:39]=1

Participants

3

Reactant 2

HCID 18766370Methyl 4-(bromomethyl)-3-fluorobenzoateHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 666194104-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxymethyl}-3-fluoro-benzoic methyl ester

Procedure

The title compound was prepared in analogy to Example 26, intermediate, from 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Example 1, intermediate c) and 4-bromomethyl-3-fluorobenzoic acid methyl ester (commercially available) to give the compound as light yellow solid (34%). MS (Turbo Spray): m/z=557.4 [M+H].

Sources & evidence

ORD record
ord-ea849200ccb84626a50190d35114329d
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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