Reaction #502099

ord-273c22f736b74f3fb7dd97c44a5839b7

Reaction equation

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
Cl
hydrochloric acid
CCOCC
diethyl ether
Cl.OB(O)c1ccc2nc(-c3ccc(Cl)cc3)cn2c1
compound
Yield 199.0%
Cl.OB(O)c1ccc2nc(-c3ccc(Cl)cc3)cn2c1
[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]boronic acid hydrochloride
Yield 199.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.STIRRINGthe mixture is stirred at ambient temperature for 24 h
  2. 2
    ConcentrationThe reaction mixture is then concentrated under reduced pressure
  3. 3
    OtherThe solid obtained
  4. 4
    Filtrationrecovered by filtration
  5. 5
    Otherdried in an oven under reduced pressure at 60° C

Procedure

3.60 g of 2-(4-chlorophenyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine are dissolved in 112 ml of acetone and 56 ml of water; 101 ml of 1N hydrochloric acid are added thereto, dropwise and with stirring, and the mixture is stirred at ambient temperature for 24 h. The reaction mixture is then concentrated under reduced pressure. The solid obtained is titurated with diethyl ether and recovered by filtration, and then dried in an oven under reduced pressure at 60° C. 3.12 g of compound are obtained.

Source

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