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2-Iodoaniline → 2-[4-(tert-Butyldimethylsilanyloxy)but-1-ynyl]phenylamine

HRID 2264698
Notes
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Reaction equation

HRID 2264698 reaction equation
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([Si:13]([O:16][CH2:17][CH2:18][C:19]#[CH:20])([CH3:15])[CH3:14])([CH3:12])([CH3:11])[CH3:10]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Si:13]([O:16][CH2:17][CH2:18][C:19]#[C:20][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4])([C:9]([CH3:10])([CH3:11])[CH3:12])([CH3:15])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 119952-IodoanilineHCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

Product 1

HCID 576757402-[4-(tert-Butyldimethylsilanyloxy)but-1-ynyl]phenylamine

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compound
Catalyst
HCID 8471TriethylamineSolvent

Procedure

2-Iodoaniline (1.76 g, 8 mmol) was dissolved in triethylamine (50 mL) and placed under N2. tert-Butylbut-3-ynyloxydimethylsilane (2.58 g, 14 mmol) was added, followed by bis(triphenylphosphine)palladium(II) chloride (30 mg, 0.042 mmol) and copper(I) iodide (7 mg, 0.036 mmol), and the reaction was stirred overnight at room temperature. Triethylamine was evaporated, and the residue was diluted with ether and filtered through Celite. The filtrate was concentrated, and the residue was purified by SiO2 chromatography (5-20% ethyl acetate/hexanes) to give the desired product. The reaction was assumed to be quantitative.

Workup

  1. customTriethylamine was evaporated
  2. additionthe residue was diluted with ether
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by SiO2 chromatography (5-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2cbee858c1c5450d8ef1b2159c6a4acc
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07855224B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes