Reacción #417928

ord-a04857228ba94c70b4842eaa912328b1

Ecuación de reacción

COC(=O)c1ncccc1CS(=O)(=O)Cc1ccccc1C(F)(F)F
3-(2-Trifluoromethyl-phenylmethanesulfonylmethyl)-pyridine-2-carboxylic acid methyl ester
C1CCOC1
tetrahydrofurane
Cl
HCl
O=S1(=O)Cc2cccnc2C(O)=C1c1ccccc1C(F)(F)F
colourless crystals
Rendimiento 37.3%
O=S1(=O)Cc2cccnc2C(O)=C1c1ccccc1C(F)(F)F
6,6-Dioxo-7-(2-trifluoromethyl-phenyl)-5,6-dihydro-thiopyrano[4,3-b]pyridin-8-ol
Rendimiento 37.3%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONdiluted with methylenehloride
  2. 2
    Extracciónextracted
  3. 3
    SecadoThe organic phase was dried with sodiumsulfate
  4. 4
    Concentraciónconcentrated

Procedimiento

To a solution of 3-(2-Trifluoromethyl-phenylmethanesulfonylmethyl)-pyridine-2-carboxylic acid methyl ester (7.58 g, 19.6 mmol) in tetrahydrofurane (160 ml) potassium tert-butoxide (2.20 g, 19.57 mmol) was added at room temperature and stirring was continued for 3.5 h. 1M HCl was added, diluted with methylenehloride and extracted. The organic phase was dried with sodiumsulfate and concentrated. Chromatography over silica with ethylacetate/cyclohexane gave 2.50 g colourless crystals (7.32 mmol).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08877683B2uspto-grants-2014_11