Triphenylphosphine → 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cycloheptyl-ethoxy}-3,5-difluoro-benzoic acid methyl ester

HRID 417140Notes

Reaction equation

HRID 417140 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]C[CH2:26][CH2:25][CH2:24]3)[CH2:14]OCC3CCCCC3)[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]=[C:42]([F:44])[C:41]([OH:45])=[C:40]([F:46])[CH:39]=1.[C:48]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:49]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH3:35][O:36][C:37](=[O:47])[C:38]1[CH:39]=[C:40]([F:46])[C:41]([O:45][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:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:49][CH2:48][CH2:28]2)=[C:42]([F:44])[CH:43]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 53847253Methyl 3,5-difluoro-4-hydroxybenzoateHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 666195254-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cycloheptyl-ethoxy}-3,5-difluoro-benzoic acid methyl ester

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-cycloheptyl-ethanol (Example 1, intermediate c), 3,5-difluoro-4-hydroxy-benzoic acid methyl ester (commercially available), triphenylphosphine and di-tert-butyl azodicarboxylate. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30). Colorless solid. MS (Turbo Spray): 575.4 (M+H).

Workup

  1. customThe compound was purified by silica gel chromatography
  2. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30)

Sources & evidence

ORD record
ord-ba80d0a25d7f485792576b0944637c49
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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