Ethyl bromoacetate → HCID 58577597, compound

HRID 587465Notes

Reaction equation

HRID 587465 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:28]3=[N:29][CH:30]=[CH:31][CH:32]=[C:27]3[N:26]([CH2:33][CH3:34])[C:25]2=[O:35])=[CH:20][CH:19]=1.[H-].[Na+].[Cl-].[Cl-].[Ca+2]>CN(C=O)C.CO>[CH2:33]([N:26]1[C:27]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[N:24]([C:21]2[CH:20]=[CH:19][C:18]([O:17][C:9]3[N:8]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[N:10]=3)=[CH:23][CH:22]=2)[C:25]1=[O:35])[CH3:34]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 5284359Calcium ChlorideHCID 585774113-[4-(1H-benzimidazol-2-yloxy)phenyl]-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 58577597HCID 58577597, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl bromoacetate (0.240 mL) was added to a solution of 3-[4-(1H-benzimidazol-2-yloxy)phenyl]-1-ethyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (400 mg) and sodium hydride (86 mg) in DMF (2 mL) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 2 h. The reaction mixture was diluted with MeOH (5 mL), and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane) to give ethyl {2-[4-(1-ethyl-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)phenoxy]-1H-benzimidazol-1-yl}acetate (480 mg) as off-white crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-468a7547eb44475cbdec88f39ba9587c
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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