Triethylamine → [4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-(3-methoxy-phenyl)-methanone

HRID 1661929Notes

Reaction equation

HRID 1661929 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[C:16]2[N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[N:13]([CH2:26][CH2:27][O:28][CH3:29])[C:12]=2[C:11]([O:30][CH3:31])=[CH:10][C:9]=1[CH:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=1)[OH:33].C(N(CC)CC)C>ClCCl.CS(C)=O>[Br:7][C:8]1[C:16]2[N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:24])[CH3:25])=[CH:19][CH:18]=3)[N:13]([CH2:26][CH2:27][O:28][CH3:29])[C:12]=2[C:11]([O:30][CH3:31])=[CH:10][C:9]=1[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH3:41])[CH:35]=1)=[O:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57772052[4-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-(3-methoxy-phenyl)-methanol

Product 1

HCID 11191900[4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-(3-methoxy-phenyl)-methanoneYield 71.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-60 °C

Procedure

To a solution of 0.16 ml oxalylchloride in 4 ml dichloromethane, 0.27 ml DMSO (in 0.8 ml dichloromethane is slowly added at −60° C. This mixture is stirred under argon at −60° C. for 0.5 h. Then 250 mg (0.463 mmol) [4-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-(3-methoxy-phenyl)-methanol (in 2 ml dichloromethane) are added and stirring is continued at −60° C. for 1 h. 1 ml triethylamine is added and the reaction mixture is allowed to warm to room temperature, poured on water and extracted (3×) with dichloromethane. 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=2:1) to afford 179 mg of the title compound as a colorless oil.

Workup

  1. stirringstirring
  2. waitis continued at −60° C. for 1 h
  3. temperatureto warm to room temperature
  4. additionpoured on water
  5. extractionextracted (3×) with dichloromethane
  6. washThe combined organic layers are washed with water (2×) and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1)

Sources & evidence

ORD record
ord-0ecdfb4b37414e069707cf86067dcf27
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

Loading…