3-Bromoaniline → 1-(t-Butyldimethylsiloxy)-4-(3-amino-phenyl)-3-butyne

HRID 1279364Notes

Reaction equation

HRID 1279364 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 222257391-(t-Butyldimethylsiloxy)-4-(3-amino-phenyl)-3-butyne

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-9608bdf016fd466a8681ccb0b6cc17b3
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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