Triphenylphosphine → HCID 66619337, compound

HRID 417139Notes

Reaction equation

HRID 417139 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.[OH:35][C:36]1[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][N:37]=1.[C:46]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:47]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[CH3:43][O:42][C:40](=[O:41])[C:39]1[CH:44]=[CH:45][C:36]([O:35][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][CH2:47][CH2:46][CH2:28]2)=[N:37][CH:38]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×HCID 178498304HCID 178498304, compound

Product 1

HCID 66619337HCID 66619337, compoundYield 78%

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 6-hydroxynicotinate (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) to give the desired compound as a colorless solid (78%). MS (Turbo Spray): m/z=540.3 [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-c08b94598e4d42739076a4c543264b2d
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

Loading…