Trifluoroacetic acid → 6-(2-(Piperidin-4-yl)ethoxy)-2-bromo-3-(3,5-difluorophenyl)-1H-inden-1-one

HRID 331347Notes

Reaction equation

HRID 331347 reaction equation
[Br:1][C:2]1[C:3](=[O:35])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)=[CH:8][CH:7]=[C:6]([O:19][CH2:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]1)[CH:5]=2.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[NH:25]1[CH2:26][CH2:27][CH:22]([CH2:21][CH2:20][O:19][C:6]2[CH:5]=[C:4]3[C:9]([C:10]([C:11]4[CH:12]=[C:13]([F:18])[CH:14]=[C:15]([F:17])[CH:16]=4)=[C:2]([Br:1])[C:3]3=[O:35])=[CH:8][CH:7]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 70313410t-Butyl 4-(2-(2-bromo-3-(3,5-difluorophenyl)-1-oxo-1H-inden-6-yloxy)ethyl)piperidine-1-carboxylate

Product 1

HCID 703150056-(2-(Piperidin-4-yl)ethoxy)-2-bromo-3-(3,5-difluorophenyl)-1H-inden-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of t-Butyl 4-(2-(2-bromo-3-(3,5-difluorophenyl)-1-oxo-1H-inden-6-yloxy)ethyl)piperidine-1-carboxylate (700 mg, 1.4 mmol) obtained in Step 1 in CH2Cl2 was added TFA (20 eq, 27 mmol). The solution was stirred for 1 h at room temperature and diluted with CH2Cl2. The mixture was basicified to with 3N aq. NaOH. The organic layer was washed with H2O and brine, dried over MgSO4, and concentrated to obtain the title compound (99%).

Workup

  1. washThe organic layer was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0599a71c46b54c3f91f05a108c3fdc3c
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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