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

HRID 1092419Notes

Reaction equation

HRID 1092419 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]

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, compoundCatalystHCID 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-64c5bdf8693241d9871d8873b1d602f2
Source dataset
uspto-grants-2012_03
Patent number
US08129424B2

Reaction notes

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