Réaction #994455

Équation de réaction

N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

product

6-Bromo-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

potassium carbonate

→

sub-title compound

6-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid, methyl ester

Solvants

DMF

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Autreprepared
2. 2
   Lavagewashed with water and brine
3. 3
   SéchageThe organics were dried over magnesium sulphate
4. 4
   Autreevaporated
5. 5
   AutreThe crude product was purified (SiO2, 50 to 70% ethyl acetate in isohexane as eluent)

Mode opératoire

A mixture of N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (4.24 g) [prepared as described in US2005020590], the product of step iii) (4.3 g), tetrakis(triphenylphosphine)palladium(0) (1.5 g) and potassium carbonate (3.54 g) in DMF (50 mL) was heated to 80° C. for 17 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organics were dried over magnesium sulphate and evaporated. The crude product was purified (SiO2, 50 to 70% ethyl acetate in isohexane as eluent) to yield the sub-title compound (2.5 g).

Source