Réaction #42328

Équation de réaction

N-{(1R,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-3-bromo-5-methylbenzamide

2-furanylboronic acid

sodium carbonate

→

title compound

N-{(1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-3-(2-furyl)-5-methylbenzamide

Solvants

dimethylformamide

chloroform

Conditions de réaction

Traitement

1. 1
   Autresparged under a flow of nitrogen for 15 minutes
2. 2
   Autreovernight
3. 3
   TempératureThe mixture is cooled to 20-25 degrees C
4. 4
   Extractionextracted with water (3×100 ml)
5. 5
   AutreThe organic phase is separated
6. 6
   Lavagewashed with saturated sodium bicarbonate (2×100 ml) and saline (100 ml)
7. 7
   Séchagedried over anhydrous sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated under reduced pressure

Mode opératoire

N-{(1R,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-3-bromo-5-methylbenzamide (X, EXAMPLE 761, 295 mg, 0.59 mmol), 2-furanylboronic acid (133 mg, 1.19 mmol) and sodium carbonate (366 mg, 2.95 mmol) are combined in dimethylformamide (5 ml) and sparged under a flow of nitrogen for 15 minutes. Tetrakis(triphenylphosphino)palladium (136 mg, 0.12 mmol) is added and the mixture heated to 100 degrees C. overnight. The mixture is cooled to 20-25 degrees C., diluted with chloroform (50 ml) and extracted with water (3×100 ml). The organic phase is separated and washed with saturated sodium bicarbonate (2×100 ml) and saline (100 ml), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue is chouromatographed (silica gel; methanol/methylene chloride, 8/92) to give the title compound, MS [M+H]+=485.3.

Source