o-Fluoro-beta-nitrostyrene → (3-(1-(2-Fluorophenyl)-2-nitroethyl)-1H-indol-6-yl)(morpholino)methanone

HRID 2361242Notes

Reaction equation

HRID 2361242 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1/[CH:25]=[CH:26]/[N+:27]([O-:29])=[O:28]>C1(C)C=CC=CC=1>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH:25]([C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[O:11])=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH2:26][N+:27]([O-:29])=[O:28]

Participants

4

Reactant 2

HCID 5383481o-Fluoro-beta-nitrostyreneHCID 39710543(1H-Indol-6-yl)(morpholino)methanone

Product 1

HCID 67994854(3-(1-(2-Fluorophenyl)-2-nitroethyl)-1H-indol-6-yl)(morpholino)methanoneYield 18.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A sealed tube containing (1H-indol-6-yl)(morpholino)methanone (0.6323 g, 2.75 mmol) and (E)-1-fluoro-2-(2-nitrovinyl)benzene (0.551 g, 3.30 mmol) in toluene (14 mL) was stirred at 150° C. for 4 days. The reaction was cooled and concentrated in vacuo to give a residue which was purified by flash chromatography using an ISCO 80 g column eluting with 0-100% EtOAc/hexanes. Appropriate fractions (100% elution) were collected and concentrated in vacuo to give the desired product (0.222 g, 0.508 mmol, 18.5% yield).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. customto give a residue which
  4. customwas purified by flash chromatography
  5. washeluting with 0-100% EtOAc/hexanes
  6. washAppropriate fractions (100% elution)
  7. customwere collected
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85088e8865114d4c80705853f01a5cba
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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