3,5-Dimethyl-4-hydroxybenzonitrile → 4-[2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-(4,4-difluoro-cyclohexyl)-ethoxy]-3,5-dimethyl-benzonitrile

HRID 417144Notes

Reaction equation

HRID 417144 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:16]3[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18][CH2:17]3)[CH2:14][OH:15])[C:11]3[CH:24]=[C:25]([F:29])[C:26]([F:28])=[CH:27][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH3:30][C:31]1[CH:32]=[C:33]([CH:36]=[C:37]([CH3:40])[C:38]=1O)[C:34]#[N:35]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:16]3[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18][CH2:17]3)[CH2:14][O:15][C:38]3[C:37]([CH3:40])=[CH:36][C:33]([C:34]#[N:35])=[CH:32][C:31]=3[CH3:30])[C:11]3[CH:24]=[C:25]([F:29])[C:26]([F:28])=[CH:27][C:10]=3[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 666192272-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-(4,4-difluoro-cyclohexyl)-ethanol

Product 1

HCID 666195364-[2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-(4,4-difluoro-cyclohexyl)-ethoxy]-3,5-dimethyl-benzonitrile

Procedure

The title compound was prepared in analogy to Example 4, intermediate, from 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-(4,4-difluoro-cyclohexyl)-ethanol, 3,5-dimethyl-4-hydroxybenzonitrile (commercially available), tri-n-butylposphine and N′N′N′N-tetramethylazodicarboxamide. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of a gradient of heptane:ethyl acetate (100:0 to 60:40). Light yellow solid (27%). MS (Turbo Spray): m/z=556.178 [M+H].

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of a gradient of heptane:ethyl acetate (100:0 to 60:40)

Sources & evidence

ORD record
ord-093c0205ee854166a02bfbbbde96a4ae
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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