Réaction #168678

Équation de réaction

iso-hexane

5-Bromo-3-chloro-pyrazin-2-ylamine

2-methyl-5-(N-morpholinylsulfonyl)phenylboronic acid

Na2CO3

→

title compound

3-Chloro-5-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-ylamine

Solvants

ethyl acetate

DCM

DME

DCM

Conditions de réaction

Traitement

1. 1
   AutreProduct is purified by reverse phase chromatography and evaporation of the clean fractions
2. 2
   Autreyields a cream solid
3. 3
   Lavagewashed with 2N NaOH (aq.) (50 ml)
4. 4
   SéchageThe organic phase is dried over magnesium sulphate
5. 5
   Filtrationfiltered
6. 6
   Autrethe solvent evaporated
7. 7
   Autreto yield an orange semi-solid
8. 8
   workup.ADDITIONis added
9. 9
   FiltrationA precipitate forms and is filtered off

Mode opératoire

5-Bromo-3-chloro-pyrazin-2-ylamine (0.600 g, 2.88 mmol), 2-methyl-5-(N-morpholinylsulfonyl)phenylboronic acid (0.821 g, 2.88 mmol), 1,1′BIS(Diphenylphosphino-ferrocene)dichloropalladium (II) complex with DCM (0.118 g, 0.14 mmol), 2N Na2CO3 (aq.) (5 ml) and DME (15 ml) are stirred together at 100° C. for 1 hour. Product is purified by reverse phase chromatography and evaporation of the clean fractions yields a cream solid. The solid is dissolved in DCM (100 ml) and washed with 2N NaOH (aq.) (50 ml). The organic phase is dried over magnesium sulphate, filtered and the solvent evaporated to yield an orange semi-solid. This is dissolved ethyl acetate (10 ml) and iso-hexane is added. A precipitate forms and is filtered off to yield the title compound as an off white solid. [M+H]+ 410.

Source