Potassium Carbonate → HCID 86609409, compound

HRID 1171642Notes

Reaction equation

HRID 1171642 reaction equation
Cl.[C:2]([S:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8]/[C:7]/1=[CH:12]\[C:13]1[CH:17]=[CH:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:14]=1)(=[O:4])[CH3:3].Br[CH:26]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[F:38])[C:27]([CH:29]1[CH2:31][CH2:30]1)=[O:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:2]([S:5][CH:6]1[CH2:11][CH2:10][N:9]([CH:26]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])[C:27]([CH:29]2[CH2:30][CH2:31]2)=[O:28])[CH2:8]/[C:7]/1=[CH:12]\[C:13]1[CH:17]=[CH:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:14]=1)(=[O:4])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 234358712-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethan-1-oneHCID 86609410HCID 86609410, compound

Product 1

HCID 86609409HCID 86609409, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-4-(acetylsulfanyl)-3-{[1-(t-butoxycarbonyl)-1H-pyrazol-3-yl]methylidene}piperidine hydrochloride (1.15 g) and 2-bromo-2-(2-fluorophenyl)-1-cyclopropylethanone (0.88 g) in N,N-dimethylformamide (20 ml) was added potassium carbonate (0.24 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:3 to 1:1) as the eluent to afford (E)-4-(acetylsulfanyl)-3-{[1-(t-butoxycarbonyl)-1H-pyrazol-3-yl]methylidene}-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidine (0.48 g, yield: 27%) as a colourless amorphous solid.

Workup

  1. temperaturecooling
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-56e5c98b5c5c4de79157dff319e16f1a
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

Loading…