Reacción #595386

ord-b32cfd92338740f69c71778beb3ab80b

Ecuación de reacción

O=C(c1c(Cl)cccc1C(F)(F)F)n1nc(Br)c2ccccc21
(3-bromo-1H-indazol-1-yl)(2-chloro-6-(trifluoro methyl)phenyl)methanone
O=C([O-])[O-].[K+].[K+]
K2CO3
O=C1OCc2cc(-c3nn(C(=O)c4c(Cl)cccc4C(F)(F)F)c4ccccc34)ccc21
title compound
O=C1OCc2cc(-c3nn(C(=O)c4c(Cl)cccc4C(F)(F)F)c4ccccc34)ccc21
5-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazol-3-yl)isobenzo furan-1 (3H)-one

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe reaction mixture was cooled to rt
  2. 2
    ExtracciónThe aqueous layer was extracted with EtOAc
  3. 3
    LavadoThe combined organic layers were washed with brine
  4. 4
    Secadodried over Na2SO4
  5. 5
    Concentraciónconcentrated
  6. 6
    OtroThe residue was purified by flash chromatography (PE:EA=4:1)

Procedimiento

(0.97 g, 2.48 mmol), (3-bromo-1H-indazol-1-yl)(2-chloro-6-(trifluoro methyl)phenyl)methanone (1.0 g, 2.48 mmol), K2CO3 (1.03 g, 7.44 mmol) and Pd(PPh3)4 (0.143 g, 0.12 mmol) were suspended in 1,4-dioxane (15 mL) and H2O (3 mL). The reaction mixture was heated at 100° C. in a microwave reactor for 2 h. The reaction mixture was cooled to rt and diluted with H2O. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (PE:EA=4:1) to afford the title compound as a pale yellow oil. LCMS (ESI) calc'd for C23H13ClF3N2O3 [M+H]+: 457. found: 457.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095583B2uspto-grants-2015_08