Cesium carbonate → {4-[3-(1-Cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-yloxymethyl]-phenoxy}-acetic acid methyl ester

HRID 1875725Notes

Reaction equation

HRID 1875725 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([F:18])[C:15]([F:17])=[CH:16][C:11]=3[N:10]=[C:9]2[C:19]2[C:20]([OH:25])=[N:21][CH:22]=[CH:23][CH:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:32][O:33][C:34](=[O:45])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43]Br)=[CH:39][CH:38]=1>CC(C)=O>[CH3:32][O:33][C:34](=[O:45])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][O:25][C:20]2[C:19]([C:9]3[N:8]([CH2:7][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[C:12]4[CH:13]=[C:14]([F:18])[C:15]([F:17])=[CH:16][C:11]=4[N:10]=3)=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67049717Acetic acid, 2-[4-(bromomethyl)phenoxy]-, methyl esterHCID 1785177063-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-ol

Product 1

HCID 67049940{4-[3-(1-Cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-yloxymethyl]-phenoxy}-acetic acid methyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3-(1-cyclohexylmethyl-5,6-difluoro-1H-benzoimidazol-2-yl)-pyridin-2-ol (58 mg, 0.17 mmol) in acetone (10 ml) was added cesium carbonate (0.085 g, 0.26 mmol) followed by (4-bromomethyl-phenoxy)-acetic acid methyl ester (49 mg, 0.19 mmol; CAS Reg. No. 104508-23-8) and the reaction mixture was refluxed for 2 h. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography using silica gel (50-60% ethyl acetate/n-hexane) to yield the desired compound as a brown solid (50%). MS (Turbo Spray): m/z=522.5 (M+H).

Workup

  1. temperature104508-23-8) and the reaction mixture was refluxed for 2 h
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9ec85166ca7e4c7cbfc6b5d27383b1da
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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