Methyl 4-(1-bromoethyl)benzoate → 4-(1-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-ethyl)-benzoic acid methyl ester

HRID 417115Notes

Reaction equation

HRID 417115 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]C3C=CC=CC=3F)[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]([CH:44](Br)[CH3:45])=[CH:40][CH:39]=1>>[CH3:35][O:36][C:37](=[O:47])[C:38]1[CH:43]=[CH:42][C:41]([CH: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)[CH3:45])=[CH:40][CH:39]=1

Participants

3

Reactant 2

HCID 12342351Methyl 4-(1-bromoethyl)benzoateHCID 461844412-(4-Chloro-phenyl)-1-[1-cyclohexyl-2-(2-fluoro-phenoxy)-ethyl]-5,6-difluoro-1H-benzoimidazole

Product 1

HCID 666195204-(1-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-ethyl)-benzoic acid methyl ester

Procedure

The title compound was prepared in analogy to Example 34, from 1-(2-bromo-1-cyclohexyl-ethyl)-2-(4-chloro-phenyl)-5,6-difluoro-1H-benzoimidazole (Example 34, intermediate) and 4-(1-bromo-ethyl)-benzoic acid methyl ester (CAS RN: 16281-97-3). The residue was purified by preparative HPLC chromatography (phenomenex gemini column) eluting with a gradient of water:acetonitrile (100:0 to 5:95). Light yellow foam (22%). MS (Turbo Spray): m/z=553.3 [M+H].

Workup

  1. customThe residue was purified by preparative HPLC chromatography (phenomenex gemini column)
  2. washeluting with a gradient of water:acetonitrile (100:0 to 5:95)

Sources & evidence

ORD record
ord-c22cf4d86d9c4ee9977a15513bfc91ae
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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