Reaction #502104

ord-57a492550bbf4289b42e35479e40b351

Reaction equation

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)c1ccc2ccn(S(=O)(=O)c3ccccc3)c2c1
2-bromo-1-[1-(phenylsulphonyl)indol-6-yl]ethanone
Br.CC1(C)OB(c2ccc3nc(-c4ccc5ccn(S(=O)(=O)c6ccccc6)c5c4)cn3c2)OC1(C)C
compound
Yield 55.5%
Br.CC1(C)OB(c2ccc3nc(-c4ccc5ccn(S(=O)(=O)c6ccccc6)c5c4)cn3c2)OC1(C)C
2-(1-Phenylsulphonyl-1H-indol-6-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)imidazo[1,2-a]pyridine hydrobromide
Yield 55.5%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe mixture is refluxed for 20 h
  2. 2
    FiltrationA precipitate forms and is recovered by filtration
  3. 3
    Washwashed with diethyl ether
  4. 4
    Otheroven-dried under reduced pressure

Procedure

1.6 g of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylamine and 2.7 g of 2-bromo-1-[1-(phenylsulphonyl)indol-6-yl]ethanone are placed in 70 ml of ethanol and the mixture is refluxed for 20 h. A precipitate forms and is recovered by filtration, washed with diethyl ether and oven-dried under reduced pressure. 2.3 g of compound are obtained.

Source

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