2-[4-(tert-Butyldimethylsilanyloxy)but-1-ynyl]phenylamine → 2-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1H-indole

HRID 491035

반응식

HRID 491035 반응식
[Si:1]([O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CN(C)C=O.[Cu]I>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[NH:19][C:14]2[C:13]([CH:12]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

참가 물질

4

반응물 1

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

생성물 1

HCID 116088002-[2-(tert-Butyldimethylsilanyloxy)ethyl]-1H-indole

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

2-[4-(tert-Butyldimethylsilanyloxy)but-1-ynyl]phenylamine (8 mmol) was heated at reflux in N,N-dimethylformamide (30 mL) with copper(I) iodide (5 mg, 0.026 mol) for 3 hours. The solvent 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, 0.88 g. 1H NMR (300 MHz, CDCl3) δ8.62 (br, 1H), 7.53 (d, J=7.5 Hz, 1H), 7.27 (d, J=7.8 Hz, 1H), 7.13-7.03 (m, 2H), 6.22 (s, 1H), 3.92 (t, J=5.7 Hz, 2H), 2.95 (t, J=5.7 Hz, 2H), 0.95 (s, 9H), 0.08 (s, 6H).

후처리

  1. customThe solvent 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-6cd0d70bc21f41698252cf02b776a717
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528262B2

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