Reacción #684958

ord-b9add24f19a340a0a032660f8b46dec8

Ecuación de reacción

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

Condiciones de reacción

Temperatura
75°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe reaction mixture was extracted with ethyl acetate
  2. 2
    Lavadowashed with water
  3. 3
    Secadodried over anhydrous magnesium sulfate
  4. 4
    Concentraciónconcentrated under reduced pressure
  5. 5
    OtroThe residue was purified by silica gel column chromatography

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07897387B2uspto-grants-2011_03