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

HRID 49992노트

반응식

HRID 49992 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9eac988936ae420badd690617bff15c8
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710069B2

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