Reacción #502098

ord-4b1cf724c7db4818a9c81626cff341bc

Ecuación de reacción

CC1(C)OB(c2ccc(N)nc2)OC1(C)C
5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylamine
O=C(CBr)c1ccc(Cl)cc1
2-bromo-1-(4-chlorophenyl)ethanone
O=C([O-])O.[Na+]
sodium hydrogen carbonate
CC1(C)OB(c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)OC1(C)C
compound
Rendimiento 93.2%
CC1(C)OB(c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)OC1(C)C
2-(4-Chlorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine
Rendimiento 93.2%

Disolventes

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.WAITThe reaction mixture is left
  2. 2
    Temperaturato cool
  3. 3
    Concentraciónconcentrated under reduced pressure
  4. 4
    Otrothe organic phase is then separated
  5. 5
    Secadodried over magnesium sulphate
  6. 6
    Otrothe solvent is then evaporated off under reduced pressure

Procedimiento

2.5 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylamine and 2.65 g of 2-bromo-1-(4-chlorophenyl)ethanone in 76 ml of n-propanol are placed in a round-bottomed flask. 1.33 g of sodium hydrogen carbonate are added thereto. The mixture is heated at 80° C. for 16 h. The reaction mixture is left to cool and concentrated under reduced pressure. The residue is taken up between water and ethyl acetate, the organic phase is then separated by settling out and dried over magnesium sulphate, and the solvent is then evaporated off under reduced pressure. 3.75 g of compound are obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08088765B2uspto-grants-2012_01