Acetic Acid → 4-(3-Fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)benzenamine

HRID 877108Notes

Reaction equation

HRID 877108 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[C:16]#[C:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].CC(O)=O>[Fe].CCO>[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:16]#[C:17][Si:18]([CH:19]([CH3:21])[CH3:20])([CH:22]([CH3:23])[CH3:24])[CH:25]([CH3:26])[CH3:27]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67504616(2-(2-(3-Fluorobenzyloxy)-5-nitrophenyl)ethynyl)triisopropylsilane2×

Product 1

HCID 675042324-(3-Fluorobenzyloxy)-3-(2-(triisopropylsilyl)ethynyl)benzenamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a flask was charged with (2-(2-(3-fluorobenzyloxy)-5-nitrophenyl)ethynyl)triisopropylsilane (compound 23.1, 472 mg, 1.11 mmole), Fe (309 mg), HOAc (4 mL) and EtOH (10 mL). The reaction mixture was refluxed for 3 h and the solvent was removed. Methylene was added and washed with aqueous NaHCO3. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with 30% EtOAc in Hexane to give the desired product as yellow crystalline. LCMS ESI(+) m/z: 398 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customthe solvent was removed
  3. additionMethylene was added
  4. washwashed with aqueous NaHCO3
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with 30% EtOAc in Hexane

Sources & evidence

ORD record
ord-837c990a8de54c74b1b9a552fa900803
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

Loading…