Cesium carbonate → Methyl 2-{3-[(tert-butoxycarbonyl)(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616159
Br[CH2:2][CH2:3][CH2:4][N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:11]=2)[C:6]1=[O:19].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:31]([O:30][C:29]([N:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:27][CH:26]=1)[CH2:2][CH2:3][CH2:4][N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:11]=2)[C:6]1=[O:19])=[O:35])([CH3:34])([CH3:33])[CH3:32]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 2741326tert-Butyl-4-methoxycarbanilateHCID 67282659Methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Produkt 1

HCID 67281624Methyl 2-{3-[(tert-butoxycarbonyl)(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylateAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.19 g, 0.60 mmol) dissolved in DMF (10 mL) was added tert-butyl (4-methoxyphenyl)carbamate (0.20 g, 0.89 mmol), tetra-n-butylammonium iodide (0.44 g, 1.19 mmol) and cesium carbonate (0.39 g, 1.19 mmol). The reaction mixture was stirred at rt for 6 h. The mixture was diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 60% EtOAc/hexanes) to afford methyl 2-{3-[(tert-butoxycarbonyl)(4-methoxyphenyl)amino]propyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.11 g, 38%). LC-MS: (FA) ES+ 467.

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic phases were then washed with water, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash silica gel chromatography (0% to 60% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a2c943e3d42949b981c06b3d9c86df78
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765773B2

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