Tetrahydrofuran → HCID 11395605, compound

HRID 1985863Notes

Reaction equation

HRID 1985863 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[CH:11][N:10]=[C:9]2[SH:20])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.Br[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C=O)C>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][CH2:37][N:10]1[CH:11]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]1=[S:20])[CH3:43]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 68320Ethyl 3-bromopropionateHCID 2733832Lithium HexamethyldisilazideHCID 178505525HCID 178505525, compound

Product 1

HCID 11395605HCID 11395605, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution 1-(4-chloro-phenyl)-5-(4-fluoro-phenyl)-1H-imidazole-2-thiol (1 eq) in DMF is added a 1M solution of lithium bis(trimethylsilyl)amide in THF (1 eq) and ethyl 3-bromopropionate (1 eq) at room temperature. The mixture is heated at 60° C. for 2 hours and cooled to room temperature. The mixture is quenched with water and extracted with ethyl acetate. The organics were dried and concentrated under vacuum. The residue is purified by chromatography on silica to give 3-(1-(4-chlorophenyl)-5-(4-fluorophenyl)-1,2-dihydro-2-thioxoimidazol-3-yl)propionic acid ethyl ester.

Workup

  1. temperaturecooled to room temperature
  2. customThe mixture is quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organics were dried
  5. concentrationconcentrated under vacuum
  6. customThe residue is purified by chromatography on silica

Sources & evidence

ORD record
ord-bf22890ce75c4e1d9048abadb68d5cd0
Source dataset
uspto-grants-2009_06
Patent number
US07547717B2

Reaction notes

Loading…