Réaction #502098

ord-4b1cf724c7db4818a9c81626cff341bc

Équation de réaction

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
Rendement 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
Rendement 93.2%

Solvants

Conditions de réaction

Température
80°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.WAITThe reaction mixture is left
  2. 2
    Températureto cool
  3. 3
    Concentrationconcentrated under reduced pressure
  4. 4
    Autrethe organic phase is then separated
  5. 5
    Séchagedried over magnesium sulphate
  6. 6
    Autrethe solvent is then evaporated off under reduced pressure

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08088765B2uspto-grants-2012_01