Reacción #595408

ord-a1e081892da74cccb542c5a9dc12af41

Ecuación de reacción

CCOC(C)=O.ClCCl
CH2Cl2 EtOAc
O=C1NCC(Cn2c3ccc(Br)cc3c3cc(Br)ccc32)O1
5-((3,6-dibromo-9H-carbazol-9-yl)methyl)oxazolidin-2-one
Ic1ccccn1
2-iodopyridine
O=C([O-])[O-].[K+].[K+]
K2CO3
O=C1OC(Cn2c3ccc(Br)cc3c3cc(Br)ccc32)CN1c1ccccn1
white solid
Rendimiento 79.4%
O=C1OC(Cn2c3ccc(Br)cc3c3cc(Br)ccc32)CN1c1ccccn1
5-((3,6-dibromo-9H-carbazol-9-yl)methyl)-3-(pyridin-2-yl)oxazolidin-2-one
Rendimiento 79.4%

Disolventes

Condiciones de reacción

Temperatura
130°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas sealed tightly in a vial and
  2. 2
    TemperaturaThe reaction mixture was cooled
  3. 3
    Lavadowashed with water 5×10 mL
  4. 4
    SecadoThe organic layer was dried over anhydrous Na2SO4
  5. 5
    Otroevaporated
  6. 6
    Otroto afford the crude product, which
  7. 7
    Lavadoas elute

Procedimiento

A mixture of 5-((3,6-dibromo-9H-carbazol-9-yl)methyl)oxazolidin-2-one (0.0195 g, 0.0460 mmol), 2-iodopyridine (0.0209 g, 0.102 mmol), CuI (0.0009 g, 0.00460 mmol), and K2CO3 (0.0058 g, 0.0418 mmol,) in 0.5 mL of DMSO was sealed tightly in a vial and heated at 130° C. for 12 hours. The reaction mixture was cooled and diluted with 20 mL EtOAc and washed with water 5×10 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using CH2Cl2/EtOAc as elute to afford 0.0183 g white solid as product, yield 79.4%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095572B2uspto-grants-2015_08