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

HRID 417128Notes

Reaction equation

HRID 417128 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][CH2:27][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.[Br:35][C:36]1[C:37]([OH:46])=[N:38][CH:39]=[C:40]([CH:45]=1)[C:41]([O:43][CH3:44])=[O:42].C1(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>>[CH3:44][O:43][C:41](=[O:42])[C:40]1[CH:45]=[C:36]([Br:35])[C:37]([O:46][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:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[N:38][CH:39]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 2764315Methyl 5-bromo-6-hydroxynicotinateHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 666193255-Bromo-6-{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 (Example 1, intermediate c), methyl 5-bromo-6-hydroxynicotinate (commercially available), triphenylphosphine and di-tert-butyl azodicarboxylate. The residue obtained after work-up was crystallized from acetonitrile. Colorless solid (86%). MS (Turbo Spray): m/z=604.3 [M+H].

Workup

  1. customThe residue obtained after work-up
  2. customwas crystallized from acetonitrile

Sources & evidence

ORD record
ord-295bf90fd98d472a8ec884e3a28ed078
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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