反应 #42328

反应方程式

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

溶剂

dimethylformamide

chloroform

反应条件

后处理

1. 1
   其他sparged under a flow of nitrogen for 15 minutes
2. 2
   其他overnight
3. 3
   温度The mixture is cooled to 20-25 degrees C
4. 4
   萃取extracted with water (3×100 ml)
5. 5
   其他The organic phase is separated
6. 6
   洗涤washed with saturated sodium bicarbonate (2×100 ml) and saline (100 ml)
7. 7
   干燥dried over anhydrous sodium sulfate
8. 8
   过滤filtered
9. 9
   浓缩concentrated under reduced pressure

实验过程

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.

来源