2-(1-Azidoethyl)-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole → 1-[3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]ethylamine

HRID 242877Notes

Reaction equation

HRID 242877 reaction equation
[N:1]([CH:4]([C:6]1[N:7]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:5])=[N+]=[N-]>CCOC(C)=O.[Pd]>[C:15]1([C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([S:21]([C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)(=[O:22])=[O:23])[C:6]=2[CH:4]([NH2:1])[CH3:5])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 866688682-(1-Azidoethyl)-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole

Product 1

HCID 681574851-[3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]ethylamineYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(1-azidoethyl)-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole (1.34 g, 3.22 mmol) and 10% Pd/C (200 mg) in EtOAc (80 mL) was degassed with a stream of nitrogen and stirred at RT under a hydrogen atmosphere for 20 h. The suspension was filtered and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) affording the title compound as a white solid (960 mg, 76%). 1H NMR (CDCl3, 400 MHz): δ 8.18 (1H, d, J=8.44 Hz), 7.73 (2H, d, J=8.44 Hz), 7.49-7.15 (10H, m), 4.72 (1H, q, J=6.96 Hz), 2.35 (3H, s), 1.45 (3H, d, J=7.40 Hz).

Workup

  1. customwas degassed with a stream of nitrogen
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-f1fc85cd97854d19bf28124f4975c2b4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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