1,2-Dichloroethane → HCID 66571215, Verbindung

HRID 83616

Reaktionsgleichung

Reaktionsgleichung von HRID 83616
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16](O)=[O:17])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[C:44]1([CH:50]([CH:52]2[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]2)[OH:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CCOCC.CCOC(C)=O.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:55]2[CH2:56][CH2:57][CH:52]([CH:50]([OH:51])[C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:53][CH2:54]2)=[O:17])=[CH:19][CH:20]=1

Komponenten

9

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 339086Phenyl-piperidin-4-yl-methanolHCID 186270691-(4-fluorobenzyl)-1H-indole-2-carboxylic acid

Produkt 1

HCID 66571215HCID 66571215, VerbindungAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The following was added sequentially to anhydrous DMF (5 mL): 1-(4-fluorobenzyl)-1H-indole-2-carboxylic acid (0.119 g, 0.443 mmol), Hunig's Base (0.232 ml, 1.329 mmol), EDC (0.093 g, 0.487 mmol), HOBT (0.075 g, 0.487 mmol), and phenyl(piperidin-4-yl)methanol (0.085 g, 0.443 mmol). The solution was stirred at room temperature for 30 h, at which time a 1:1 solution of EtOAc:Et2O was added and washed with 10% aq. Na2CO3. The organic solution was dried with MgSO4 and concentrated in vacuo to give a residue that was purified by silica gel chromatography (45 g silica, 80% EtOAc/Hexanes) to give 67 mg of the title compound.

Aufarbeitung

  1. washwashed with 10% aq. Na2CO3
  2. dry with materialThe organic solution was dried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give a residue that
  5. customwas purified by silica gel chromatography (45 g silica, 80% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f43753a895c049a991e7334cb68c5904
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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