Reaction #502097

ord-168cdef8280448c485a0f1aa1909b388

Reaction equation

[BH4-].[Na+]
sodium borohydride
O=Cc1ccc(-c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)o1
5-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-carbaldehyde
OCc1ccc(-c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)o1
compound
Yield 37.3%
OCc1ccc(-c2ccc3nc(-c4ccc(Cl)cc4)cn3c2)o1
{5-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-yl}methanol
Yield 37.3%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe solvent is then evaporated off under reduced pressure
  2. 2
    OtherThe organic phase is separated
  3. 3
    Dryingdried over sodium sulphate
  4. 4
    Concentrationconcentrated under reduced pressure

Procedure

122 mg of sodium borohydride are added, in small portions, to 104 mg of 5-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]furan-2-carbaldehyde dissolved in 20 ml of methanol. The mixture is subsequently stirred at ambient temperature for 2 hours, and the solvent is then evaporated off under reduced pressure. The residue is taken up between dichloromethane and water. The organic phase is separated, dried over sodium sulphate and concentrated under reduced pressure. 39 mg of compound are obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08088765B2uspto-grants-2012_01