1,2-Dichloroethane → 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid, 3,5-difluorobenzylamide

HRID 16627

Reaktionsgleichung

Reaktionsgleichung von HRID 16627
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18]([OH:20])=O)=[C:9]1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[F:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([F:45])[CH:44]=1)[CH2:40][NH2:41]>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[F:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([F:45])[CH:44]=1)[CH2:40][NH:41][C:18]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]=1[CH3:21])=[O:20]

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1452113,5-DifluorobenzylamineHCID 497872521-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid2×

Produkt 1

HCID 248041181-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid, 3,5-difluorobenzylamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid (Compound 2, 205 mg, 0.73 mmol) in CH2Cl2 (5 ml) and DMF (3 ml) was added EDC (211 mg, 1.1 mmol), HOBT (149 mg, 1.1 mmol) and 3,5-difluorobenzylamine (260 μl, 2.2 mmol). The mixture was stirred at room temperature for 16 h, diluted with EtOAc, and washed with 1M HCl, and brine, and dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (30% to 50% EtOAc-hexanes) to yield 1-benzyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid, 3,5-difluorobenzylamide (Compound 3) as a beige solid.

Aufarbeitung

  1. washwashed with 1M HCl, and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel (30% to 50% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7a9e2327eeae4ef0891cfeb4d4e60298
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737173B2

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