Formate → N,N-Diethyl-3-(3-Phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)propionamide

HRID 644549Notes

Reaction equation

HRID 644549 reaction equation
C([O-])=O.[CH2:4]([N:6]([CH2:30][CH3:31])[C:7](=[O:29])[CH:8]=[CH:9][C:10]1[C:18]2[N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[N:15][C:14]=2[CH:13]=[C:12]([C:25]([F:28])([F:27])[F:26])[CH:11]=1)[CH3:5]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].CS(C)=O>[CH2:30]([N:6]([CH2:4][CH3:5])[C:7](=[O:29])[CH2:8][CH2:9][C:10]1[C:18]2[N:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:16]=[N:15][C:14]=2[CH:13]=[C:12]([C:25]([F:27])([F:28])[F:26])[CH:11]=1)[CH3:31]

Participants

5

Reactant 2

HCID 283Formate2×HCID 68679532HCID 68679532, compound

Product 1

HCID 68679691N,N-Diethyl-3-(3-Phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)propionamide

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Alumina supported formate was prepared according to the procedure of Danks and Desai (T. N. Danks and B. Desai, Green Chemistry, 2002, 4, 179-180). A Smith Process Vial™ was loaded with alumina supported formate (0.5 g), Wilkinson's catalyst (0.5 mg), N,N-diethyl-3-(3-phenyl-6-trifluoromethyl-3H-benzimidazol-4-yl)acrylamide (0.064 mmol, 25 mg) and dimethylsulphoxide (0.5 ml) and was irradiated for 600 s at 180° C. using a Personal Chemistry Smith Creator™ microwave. The mixture was filtered to remove the solid support and the filtrate was purified by LCMS to give, after evaporation, the title compound as a solid (7.8 mg, 31%), m/z 390.0 (M+H)+.

Workup

  1. customwas prepared
  2. customwas irradiated for 600 s at 180° C.
  3. filtrationThe mixture was filtered
  4. customto remove the solid support
  5. customthe filtrate was purified by LCMS
  6. customto give
  7. customafter evaporation

Sources & evidence

ORD record
ord-f2302d38c54e4a279d503166b3412e9e
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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