Reaktion #684958

ord-b9add24f19a340a0a032660f8b46dec8

Reaktionsgleichung

O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
COC(C)(C)OC
2,2-Dimethoxypropane
CC1(C)C2CCC1(CS(=O)(=O)O)C(=O)C2
10-camphorsulfonic acid
CN(C)C=O
dimethylformamide
CC1(C)OCC(C#Cc2ccc(Cc3nccc4ccccc34)cc2)O1
title compound
CC1(C)OCC(C#Cc2ccc(Cc3nccc4ccccc34)cc2)O1
1-{4-[2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-ethynyl]benzyl}-isoquinoline

Reaktionsbedingungen

Temperatur
75°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionthe reaction mixture was extracted with ethyl acetate
  2. 2
    Waschenwashed with water
  3. 3
    Trocknendried over anhydrous magnesium sulfate
  4. 4
    Einengenconcentrated under reduced pressure
  5. 5
    SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

2,2-Dimethoxypropane (0.36 ml), 10-camphorsulfonic acid (43 mg), and molecular sieves (4 Å) were added to a solution of the compound of Example B109 (34 mg) in dimethylformamide (2 ml), and this reaction mixture was stirred at 75° C. for 9 hours. After an saturated aqueous sodium carbonate solution was added, the reaction mixture was extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (14 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07897387B2uspto-grants-2011_03