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

HRID 491035

Reaction equation

HRID 491035 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6cd0d70bc21f41698252cf02b776a717
Source dataset
uspto-grants-2009_05
Patent number
US07528262B2

Linked notes

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