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

HRID 49992Notes

Reaction equation

HRID 49992 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-9eac988936ae420badd690617bff15c8
Source dataset
uspto-grants-2004_03
Patent number
US06710069B2

Reaction notes

Loading…