Iodoethane → isopropyl 2-(3-(ethyl(6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate

HRID 1051101Notes

Reaction equation

HRID 1051101 reaction equation
[CH2:1](I)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:25]=[C:24]3[C:20]([CH2:21][CH2:22][CH:23]3[NH:26][C:27]3[CH:28]=[C:29]([CH:38]=[CH:39][CH:40]=3)[O:30][CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1>C(#N)C>[CH2:1]([N:26]([CH:23]1[C:24]2[C:20](=[CH:19][CH:18]=[C:17]([C:13]3[CH:14]=[CH:15][CH:16]=[C:11]([F:10])[CH:12]=3)[CH:25]=2)[CH2:21][CH2:22]1)[C:27]1[CH:28]=[C:29]([CH:38]=[CH:39][CH:40]=1)[O:30][CH2:31][C:32]([O:34][CH:35]([CH3:36])[CH3:37])=[O:33])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 118161547isopropyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate

Product 1

HCID 118161553isopropyl 2-(3-(ethyl(6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetateYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl iodide (45 mg, 0.286 mmol) and potassium carbonate (8 mg, 0.057 mmol) were added to a solution of isopropyl 2-(3-((6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate (12 mg, 0.029 mmol) and acetonitrile (2 mL) in a 50 mL round bottom flask at room temperature. The mixture was then heated to reflux and allowed to stir overnight. The solution was quenched with saturated ammonium chloride (5 mL) and extracted with ethyl acetate (50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by preparative TLC (1000 mm thickness, 50% ethyl acetate/hexanes) to afford 7 mg (55%) of isopropyl 2-(3-(ethyl(6-(3-fluorophenyl)-2,3-dihydro-1H-inden-1-yl)amino)phenoxy)acetate.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux
  3. customThe solution was quenched with saturated ammonium chloride (5 mL)
  4. extractionextracted with ethyl acetate (50 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude residue was purified by preparative TLC (1000 mm thickness, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bf31d92a686e436aac8174ffe119b242
Source dataset
uspto-grants-2016_07
Patent number
US09388153B2

Reaction notes

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