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

HRID 896291ノート

反応式

HRID 896291 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8b70ae7b4dbc475385bc873cef700b32
出典データセット
uspto-grants-2005_07
特許番号
US06919354B2

反応ノート

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