3-Bromoaniline → HCID 22225739, compound

HRID 366510

Reaction equation

HRID 366510 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]#[CH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C(N)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:8]([CH2:9][CH2:10][C:11]#[C:12][C:14]1[CH:20]=[CH:19][CH:18]=[C:16]([NH2:17])[CH:15]=1)[Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 115623-BromoanilineHCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

Product 1

HCID 22225739HCID 22225739, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8007ButylamineSolvent

Procedure

A mixture of 1-(t-butyldimethylsilyloxy)-3-butyne (10 mmol) and m-bromoaniline (10 mmol) in n-butylamine (50 mL) under a nitrogen atmosphere is treated with tetrakis(triphenylphosphine)palladium (0) (0.17 g) and then heated to reflux for 18 hr. After removing the solvent in vacuo, the residue is dissolved in CH2Cl2 and washed with saturated NaHCO3. The combined organic solution is dried over magnesium sulfate, filtered and evaporated to give the above described silyl protected adduct.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hr
  3. customAfter removing the solvent in vacuo
  4. dissolutionthe residue is dissolved in CH2Cl2
  5. washwashed with saturated NaHCO3
  6. dry with materialThe combined organic solution is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give the

Sources & evidence

ORD record
ord-2bffa424f5384ed486a6d8f0e064a4a9
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Linked notes

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