Triethylamine → 3-(5-Bromo-1-oxoisoindolin-2-yl)-3-methylpiperidine-2,6-dione

HRID 63416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63416
CO[C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1[CH2:11]Br.Br.[NH2:15][C:16]1([CH3:24])[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:17]1=[O:23].C(N(CC)CC)C>CN(C)C=O>[Br:10][C:7]1[CH:6]=[C:5]2[C:4](=[CH:9][CH:8]=1)[C:3](=[O:13])[N:15]([C:16]1([CH3:24])[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:17]1=[O:23])[CH2:11]2

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoateHCID 666431033-Amino-3-methyl-piperidine-2,6-dione hydrobromide

Produkt 1

HCID 690515003-(5-Bromo-1-oxoisoindolin-2-yl)-3-methylpiperidine-2,6-dioneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A stirred mixture of 4-bromo-2-bromomethyl-benzoic acid methyl ester (3.0 g, 10.0 mmol), 3-amino-3-methyl-piperidine-2,6-dione hydrobromide (2.2 g, 10.0 mmol) and triethylamine (2.0 g, 20 mmol) in N,N-dimethylformamide (10 mL) was heated to 90° C. under nitrogen. After 1 h, the mixture was cooled to rt and the solvent was removed in vacuo. The crude residue was purified by column chromatography (95:5 CH2Cl2: MeOH) providing 3-(5-bromo-1-oxo-1,3-dihydro-isoindol-2-yl)-3-methyl-piperidine-2,6-dione (2.0 g, 61% yield); 1H NMR (DMSO-d6) δ 1.67 (s, 3H), 1.87-1.93 (m, 1H), 2.54-2.80 (m, 3H), 4.64 (d, J=17.9 Hz, 1H), 4.73 (d, J=17.9 Hz, 1H), 7.58 (d, J=8.1 Hz, 1H), 7.69 (dd, J=8.1, 1.5 Hz, 1H), 7.88 (d, J=1.5 Hz, 1H), 10.89 (s, 1H).

Aufarbeitung

  1. temperaturethe mixture was cooled to rt
  2. customthe solvent was removed in vacuo
  3. customThe crude residue was purified by column chromatography (95:5 CH2Cl2: MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-bef9fef24e2147fa964ea18d0cc41544
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447070B2

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