Pyridine → 1-(2-(2-(5-bromo-pyridin-2-yl)-6-(4-methanesulfonyl-phenoxy)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13345Notes

Reaction equation

HRID 13345 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].N1C=CC=CC=1.[Br:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[NH:25][C:24]3[CH:26]=[C:27]([CH:41]4[CH2:45][CH2:44][CH2:43][NH:42]4)[C:28]([O:30][C:31]4[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:39])=[O:38])=[CH:33][CH:32]=4)=[CH:29][C:23]=3[N:22]=2)=[N:19][CH:20]=1>C(Cl)(Cl)Cl>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[NH:25][C:24]3[CH:26]=[C:27]([CH:41]4[CH2:45][CH2:44][CH2:43][N:42]4[C:1](=[O:3])[CH3:2])[C:28]([O:30][C:31]4[CH:36]=[CH:35][C:34]([S:37]([CH3:40])(=[O:38])=[O:39])=[CH:33][CH:32]=4)=[CH:29][C:23]=3[N:22]=2)=[N:19][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 231454112-(5-bromo-pyridin-2-yl)-5-(4-methanesulfonyl-phenoxy)-6-pyrrolidin-2-yl-1H-benzimidazole

Product 1

HCID 112498721-(2-(2-(5-bromo-pyridin-2-yl)-6-(4-methanesulfonyl-phenoxy)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.050 ml of acetic anhydride was added to a pyridine (2 ml) solution of 220 mg of 2-(5-bromo-pyridin-2-yl)-5-(4-methanesulfonyl-phenoxy)-6-pyrrolidin-2-yl-1H-benzimidazole, and the reaction liquid was stirred at room temperature for 30 minutes. The reaction liquid was diluted with chloroform, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol/aqueous ammonia=50/1/0.1) to obtain the entitled compound as a pale brown solid.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with water and saturated saline in order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol/aqueous ammonia=50/1/0.1)

Sources & evidence

ORD record
ord-6157a008fecb49d1997f0c1b6314357c
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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