Triphenylphosphine → 2-[1-(Benzenesulfonyl)indol-4-yl]oxyethanamine

HRID 896291Notes

Reaction equation

HRID 896291 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:19][CH2:20][CH2:21][N:22]=[N+]=[N-])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([O:19][CH2:20][CH2:21][NH2:22])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 120184382-{[1-(Phenylsulfonyl)-1H-indole-4-yl]oxy}ethylazide

Product 1

HCID 102678372-[1-(Benzenesulfonyl)indol-4-yl]oxyethanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-{[1-(phenylsulfonyl)-1H-indole-4-yl]oxy}ethylazide (3.3 g, 9.6 mmol) and triphenylphosphine (3.67 g, 14 mmol) in tetrahydrofuran and water is stirred under nitrogen for 24 hr at room temperature and filtered. The filtrate is concentrated in vacuo and the resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 8.5/1.5/0.05) to afford the title compound as an off-white solid, 2.54 g (80%), mp 71-73° C., identified by NMR and mass spectral analyses.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo
  3. customthe resultant residue is purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH: 8.5/1.5/0.05)

Sources & evidence

ORD record
ord-8b70ae7b4dbc475385bc873cef700b32
Source dataset
uspto-grants-2005_07
Patent number
US06919354B2

Reaction notes

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