Potassium Carbonate → 3-(3,5-difluorophenyl)-5-[2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy]-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331397Notes

Reaction equation

HRID 331397 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=3)[C:11](=[O:19])[C:10]=2[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH3:32][S:33]([N:36]1[CH2:41][CH2:40][N:39]([CH2:42][CH2:43]OS(C)(=O)=O)[CH2:38][CH2:37]1)(=[O:35])=[O:34]>CN(C=O)C.O>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:43][CH2:42][N:39]4[CH2:40][CH2:41][N:36]([S:33]([CH3:32])(=[O:34])=[O:35])[CH2:37][CH2:38]4)[CH:16]=3)[C:11](=[O:19])[C:10]=2[C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2727497Methylsulfonyl 2-(4-(methylsulfonyl)piperazin-1-yl)ethyl etherHCID 703127873-(3,5-Difluorophenyl)-5-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one

Product 1

HCID 703157393-(3,5-difluorophenyl)-5-[2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy]-2-(pyridin-3-yl)-1H-inden-1-oneYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(3,5-difluorophenyl)-5-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one (60 mg, 0.18 mmol) obtained in Step 5 of Example 128 in DMF (2 mL) was added K2CO3(75 mg, 0.54 mmol) and methylsulfonyl 2-(4-(methylsulfonyl)piperazin-1-yl)ethyl ether (77 mg, 0.27 mmol). The mixture was heated to 80° C. for 3 h and cooled to room temperature. The resulting solution was diluted with H2O (5 mL) and extracted with EtOAc (5 mL×3). The extracts were washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (2% MeOH/CH2Cl2) to afford the title compound (65 mg, 69%).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc (5 mL×3)
  3. washThe extracts were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9a019472c8cb4efa9ce7210cc177bce1
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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