Acetonitrile → 5-[{1-(3-chloropropyl)-1H-benzoimidazol-2-yl}methyl]-2-methyl-5H-furo[3,2-c]pyridin-4-one

HRID 69050Notes

Reaction equation

HRID 69050 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[CH:16]=[CH:15][C:14]2[O:17][C:18]([CH3:20])=[CH:19][C:13]=2[C:12]1=[O:21].Br[CH2:23][CH2:24][CH2:25][Cl:26].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[Cl:26][CH2:25][CH2:24][CH2:23][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[CH:16]=[CH:15][C:14]2[O:17][C:18]([CH3:20])=[CH:19][C:13]=2[C:12]1=[O:21]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 669600755-(1H-Benzimidazol-2-ylmethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one

Product 1

HCID 706569625-[{1-(3-chloropropyl)-1H-benzoimidazol-2-yl}methyl]-2-methyl-5H-furo[3,2-c]pyridin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(1H-Benzimidazol-2-ylmethyl)-2-methyl-5H-furo[3,2-c]pyridine-4-one (0.75 g), 1-bromo-3-chloropropane (1.3 ml), and potassium carbonate (0.95 g) were added to 50% hydrous acetonitrile (16 ml). The mixture was heated overnight under reflux. The reaction mixture was cooled to room temperature. Water was added thereto, followed by extraction by ethyl acetate. The organic layer was dried over sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1). The purified product was condensed to dryness under reduced pressure to give the title compound (0.18 g) as a colorless oily matter.

Workup

  1. temperatureThe mixture was heated overnight
  2. temperatureunder reflux
  3. extractionfollowed by extraction by ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate, and condensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)
  6. customcondensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-96eecc2af15b44dbbcc4f8255cc0a8a4
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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