Sodium Hydroxide → 2-(7-Fluoro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester

HRID 1098613

Reaktionsgleichung

Reaktionsgleichung von HRID 1098613
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11]N(C)C.[CH2:15]([O:17][C:18](=[O:28])[CH:19]([NH:25][CH:26]=[O:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:16].[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:23]([O:22][C:20](=[O:21])[C:19]([CH2:11][C:7]1[C:6]2[C:10](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=2)[NH:9][CH:8]=1)([NH:25][CH:26]=[O:27])[C:18]([O:17][CH2:15][CH3:16])=[O:28])[CH3:24]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 80617Diethyl formamidomalonateHCID 249051291-(7-Fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine

Produkt 1

HCID 575633012-(7-Fluoro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl esterAusbeute 101,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of (7-fluoro-1H-indol-3-ylmethyl)-dimethyl-amine (550 mg, 0.0028 mol.), 2-formylamino-malonic acid diethyl ester (640 mg, 0.0031 mol.), and NaOH (30 mg) in toluene (20 mL) under argon was refluxed for 3 days. The reaction mixture was concentrated and purified by column chromatography on silica gel using 40% ethyl acetate-hexane to give 2-(7-Fluoro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester (1.0 gm, 99%): mp 164-166° C., 1H NMR (500 MHz, CDCl3): 1.28 (t, J=7.5 Hz, 6H), 3.87 (s, 2H), 4.17-4.31 (m, 4H), 6.80 (s, 1H), 6.86-6.89 (dd, J=8.0 and 8.0 Hz, 1H), 6.97-7.01 (m, 2H), 7.27 (s, 1H), 8.18 (d, J=1.5 Hz, 1H), 8.27 (s, 1H).

Aufarbeitung

  1. temperaturewas refluxed for 3 days
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography on silica gel using 40% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-b990747552a94b50a4ca2dd5596c7ae6
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143300B2

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