Réaction #684958

ord-b9add24f19a340a0a032660f8b46dec8

Équation de réaction

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

Conditions de réaction

Température
75°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionthe reaction mixture was extracted with ethyl acetate
  2. 2
    Lavagewashed with water
  3. 3
    Séchagedried over anhydrous magnesium sulfate
  4. 4
    Concentrationconcentrated under reduced pressure
  5. 5
    AutreThe residue was purified by silica gel column chromatography

Mode opératoire

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07897387B2uspto-grants-2011_03