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

HRID 417136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 417136
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[C:14](C)(OC3C=CC(C4NN=NN=4)=CC=3)C)[C:11]3[CH:35]=[C:36]([F:40])[C:37]([F:39])=[CH:38][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH3:41][O:42][C:43](=[O:53])[C:44]1[CH:49]=[C:48]([F:50])[C:47]([OH:51])=[C:46]([F:52])[CH:45]=1.[C:54]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH3:41][O:42][C:43](=[O:53])[C:44]1[CH:45]=[C:46]([F:52])[C:47]([O:51][CH2:14][CH:13]([N:12]2[C:11]3[CH:35]=[C:36]([F:40])[C:37]([F:39])=[CH:38][C:10]=3[N:9]=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:54])[CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[C:48]([F:50])[CH:49]=1

Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 53847253Methyl 3,5-difluoro-4-hydroxybenzoateHCID 178458272HCID 178458272, Verbindung2×

Produkt 1

HCID 666192204-{2-[2-(4-Chloro-2-methyl-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-3,5-difluoro-benzoic acid methyl ester

Versuchsvorschrift

The compound was prepared in analogy to Example 4, intermediate, from 2-[2-(4-chloro-2-methyl-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (example 123, intermediate b), 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). Light yellow foam (37%). MS (Turbo Spray): m/z=575.4 [M+H].

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-629e641a25194c89ae300ce4dac9d268
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088930B2

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