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

HRID 1092419

반응식

HRID 1092419 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-64c5bdf8693241d9871d8873b1d602f2
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129424B2

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