Benzyl Bromide → 5-Bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic Acid Benzyl Ester

HRID 342799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342799
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[C:6]([C:21]([OH:23])=[O:22])=[CH:5]2.C(=O)(O)[O-].[Na+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O.C(OCC)(=O)C>[CH2:29]([O:22][C:21]([C:6]1[N:7]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)=[O:23])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 540736965-Bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic Acid

Produkt 1

HCID 538099935-Bromo-1-(4-nitro-benzyl)-1H-indole-2-carboxylic Acid Benzyl EsterAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 5-bromo-1-(4-nitro-benzyl)-1-H-indole-2-carboxylic acid (1.66 g, 4.43 mmol) and sodium bicarbonate (0.93 g, 11.1 mmol) in dry dimethylformamide at room temperature under nitrogen was added benzyl bromide (2.275 g, 1.58 ml, 13.3 mmol). The reaction mixture was warmed to about 60° C. for about 16 hours and then the mixture was cooled, diluted with ethyl acetate, washed with dilute sodium bicarbonate solution and brine, dried over sodium sulfate, and concentrated in vacuo. The resulting residue was flash chromatographed on silica (60 g) with 20% ethyl acetate/hexanes. The purified product was taken up in hot toluene/heptane and allowed to crystallize slowly. The light brown solid was washed with heptane and dried in air, then under vacuum to give the title compound (1.73 g).

Aufarbeitung

  1. temperaturethe mixture was cooled
  2. washwashed with dilute sodium bicarbonate solution and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica (60 g) with 20% ethyl acetate/hexanes
  6. customto crystallize slowly
  7. washThe light brown solid was washed with heptane
  8. customdried in air

Quellen und Nachweise

ORD-Eintrag
ord-5aa6af41d29d4b00bd0d5cf1cef5e596
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859044

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