Phenethyl bromide → HCID 51001890, compound

HRID 331311

Reaction equation

HRID 331311 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([OH:18])=[CH:15][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+].Br[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CC#N.CCOC(C)=O>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:15][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 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 703174323-(3,5-difluorophenyl)-6-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one

Product 1

HCID 51001890HCID 51001890, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3,5-difluorophenyl)-6-hydroxy-2-(pyridin-3-yl)-1H-inden-1-one (0.15 mol, 50 mg) obtained in Step 1 in CH3CN was added K2CO3(1.5 eq). 1-(2-bromoethyl)benzene (1.5 eq) was added dropwise and the resulting mixture was heated to reflux for 3 d. The reaction was cooled to room temperature and diluted with EtOAc. The organic layer was washed with H2O, dried over MgSO4, and concentrated in vacuo to obtain the title compound (30%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 d
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86b7d8860c7e4b418708a2ff8c0b2c8a
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Linked notes

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