Di-tert-butyl azodicarboxylate → 6-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-nicotinic acid methyl ester

HRID 417074Notes

Reaction equation

HRID 417074 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][CH2:19][CH2:18][CH2:17]3)[CH2:14][OH:15])[C:11]3[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH3:28][O:29][C:30](=[O:39])[C:31]1[CH:36]=[C:35](Cl)[C:34](O)=[N:33][CH:32]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH3:28][O:29][C:30](=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([O:15][CH2:14][CH:13]([N:12]2[C:11]3[CH:22]=[C:23]([F:27])[C:24]([F:26])=[CH:25][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:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)=[N:33][CH:32]=1

Participants

4

Reactant 3

HCID 97268Di-tert-butyl azodicarboxylateHCID 666193102-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanolHCID 178498848HCID 178498848, compound

Product 1

HCID 666193086-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-nicotinic 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-cyclohexyl-ethanol (Ex. 1, int. c) and 5-chloro-6-hydroxy-nicotinic acid methyl ester and replacing di-ethyl azodicarboxylate by di-tert-butyl azodicarboxylate. White solid (83%). MS (Turbo Spray): m/z=560.3 [M+H].

Sources & evidence

ORD record
ord-e5c8baa863e444c7a57a0a85a4ae4c0b
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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