Dimethylformamide → HCID 59170811, compound

HRID 1362689Notes

Reaction equation

HRID 1362689 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][C:20]=1[N:21]1[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]1)/[CH:11]=[C:12]1/[C:13](=[O:17])[NH:14][CH2:15][CH2:16]/1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:37][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][C:45]=1[F:46])[CH2:41]Br>C(OCC)(=O)C.O>[F:37][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][C:45]=1[F:46])[CH2:41][N:14]1[CH2:15][CH2:16]/[C:12](=[CH:11]\[C:10]2[CH:18]=[CH:19][C:20]([N:21]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]3)=[C:8]([O:7][CH3:6])[CH:9]=2)/[C:13]1=[O:17]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 2733832Lithium HexamethyldisilazideHCID 66960729HCID 66960729, compound

Product 1

HCID 59170811HCID 59170811, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a DMF (6.0 mL) solution of (E)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)pyrrolidin-2-one (100 mg), lithium bis(trimethylsilyl)amide (1M hexane solution, 0.53 mL) was added at 0° C., and the reaction solution was agitated for 30 minutes at 0° C. 3,4-difluorobenzylbromide (0.060 mL) was added to this solution at 0° C., and that reaction solution was agitated at room temperature for 1 hour. The reaction solution was added to iced water and ethyl acetate, and the organic layer was partitioned. The obtained organic layer was washed with a saturated salt solution, and it concentrated under reduced pressure after dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system), and 80 mg of the title compound was obtained.

Workup

  1. stirringthat reaction solution was agitated at room temperature for 1 hour
  2. customthe organic layer was partitioned
  3. washThe obtained organic layer was washed with a saturated salt solution, and it
  4. concentrationconcentrated under reduced pressure
  5. dry with materialafter dried over anhydrous magnesium sulfate
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-4705abe3e2254b1fac105b13673b424e
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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