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

HRID 417069Notes

Reaction equation

HRID 417069 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.[CH2:28]([O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[C:34](O)[CH:33]=1)[CH3:29].N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH2:28]([O:30][C:31](=[O:40])[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[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)[CH:33]=1)[CH3:29]

Participants

4

Reactant 3

HCID 97268Di-tert-butyl azodicarboxylateHCID 157454893-HYDROXY-4-METHYLBENZOIC ACID ETHYL ESTERHCID 666193102-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol

Product 1

HCID 666195213-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-4-methyl-benzoic acid ethyl 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 3-hydroxy-4-methyl-benzoic acid ethyl ester and replacing di-ethyl azodicarboxylate by di-tert-butyl azodicarboxylate. White solid (16%). MS (Turbo Spray): m/z=539.2 [M+H].

Sources & evidence

ORD record
ord-6177c7a6155f4fb9af1a68cd5d7f7949
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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