1,2-Dichloroethane → HCID 50919245, Verbindung

HRID 1851892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851892
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=O)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.Cl.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]([NH2:33])[CH3:32])=[CH:27][CH:26]=1)([O-:24])=[O:23].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([NH:33][C@H:31]([C:28]4[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=4)[CH3:32])=[O:18])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:19][CH:20]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16212176(1S)-1-(4-Nitrophenyl)ethan-1-amine--hydrogen chloride (1/1)HCID 63749115HCID 63749115, Verbindung

Produkt 1

HCID 50919245HCID 50919245, VerbindungAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-bromobenzyl)-1H-indole-5-carboxylic acid (1.03 g, 3.1 mmol, 1 equiv) in DMF (30 mL) were added the (S)-1-(4-nitrophenyl)ethanamine hydrochloride (695 mg, 3.4 mmol, 1.1 equiv), DIEA (600 μL, 3.4 mmol, 1.1 equiv), HOBt (525 mg, 3.4 mmol, 1.1 equiv) and EDC (658 mg, 3.4 mmol, 1.1 equiv). After stirring 4 h at room temperature, the mixture was diluted with AcOEt and washed with a 0.5 N HCl aqueous solution, a saturated NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuo. The crude was purified by flash chromatography (Hexane/AcOEt 1/1) to afford a yellow powder (1.3 g, 2.7 mmol, 87%). ESI-MS (m/z): 478/480 [M+H]+.

Aufarbeitung

  1. washwashed with a 0.5 N HCl aqueous solution
  2. dry with materiala saturated NaHCO3 solution and brine, dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by flash chromatography (Hexane/AcOEt 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-13a79cfb971c46cd98f9d6ea70905d84
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957093B2

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