Cesium carbonate → 2-(4-Chloro-2-cyclohexylmethoxy-phenyl)-1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazole

HRID 1875749Notes

Reaction equation

HRID 1875749 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[N:13]([CH2:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[C:12]3[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:11]=3[N:10]=2)=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[N:13]([CH2:14][CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[C:12]3[CH:21]=[C:22]([F:26])[C:23]([F:25])=[CH:24][C:11]=3[N:10]=2)=[C:6]([O:8][CH2:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 1363784785-chloro-2-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-phenol

Product 1

HCID 582092452-(4-Chloro-2-cyclohexylmethoxy-phenyl)-1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazoleYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the solution of 5-chloro-2-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-phenol (Example 19, intermediate a) (98 mg, 0.26 mmol) in acetone (10 ml) was added cesium carbonate (127 mg, 0.39 mmol) followed by bromomethyl-cyclohexane (42 mg, 0.31 mmol; CAS Reg. No. 2550-36-9) and the reaction was refluxed for 12 h. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The crude material was purified by column chromatography using silica gel (30-40% ethyl acetate/n-hexane) to afford the desired product as an off-white powder (56%). MS (Turbo Spray): m/z=473.0 (M+H).

Workup

  1. temperature2550-36-9) and the reaction was refluxed for 12 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-5f6ec262aab8464293a5ad05256f3818
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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