Sodium hydride → HCID 11751849, compound

HRID 1661894Notes

Reaction equation

HRID 1661894 reaction equation
[H-].[Na+].[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([CH2:17][CH2:18][O:19][CH3:20])[C:15]3[C:21]([O:32][CH3:33])=[CH:22][CH:23]=[C:24]([C:25]4[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=4)[C:14]=3[N:13]=2)=[CH:8][CH:7]=1)([CH3:5])[CH3:4]>CN(C=O)C>[CH:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:16]([CH2:17][CH2:18][O:19][CH3:20])[C:15]3[C:21]([O:32][CH3:33])=[CH:22][CH:23]=[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:17][CH2:18][O:19][CH3:20])[CH:26]=4)[C:14]=3[N:13]=2)=[CH:10][CH:11]=1)([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 11407388HCID 11407388, compound

Product 1

HCID 11751849HCID 11751849, compoundYield 170.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 mg (0.2 mmol) NaH is added to a solution of 70 mg (0.173 mmol) 3-[2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-4-yl]-phenol in 2 ml DMF. This mixture is stirred at room temperature for 1 h. After that 28 mg (0.207 mmol) 2-(bromoethyl)-methyl ether is added and stirring is continued for another 3 h. The reaction mixture is poured on water and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 70 mg of the title compound as a colorless oil.

Workup

  1. stirringstirring
  2. waitis continued for another 3 h
  3. additionThe reaction mixture is poured on water
  4. extractionextracted (3×) with ethyl acetate
  5. washThe combined organic layers are washed with water (2×) and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-a7763c4d25024f53878cfa9b0ff327d7
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

Loading…