反应 #1914871

反应方程式

K2CO3

5-2

5-(5-Bromo-pyridin-2-yl)-pentanoic acid ethyl ester

5-5

2-But-3-enyl-isoindole-1,3-dione

9-BBN

→

5-6

5-{5-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-pyridin-2-yl}-pentanoic acid ethyl ester

溶剂

ethyl acetate

DMF

THF

反应条件

后处理

1. 1
   workup.ADDITIONa premixed
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 18 hours at 70° C.
3. 3
   温度cooled
4. 4
   洗涤washed with water and brine
5. 5
   干燥dried over MgSO4
6. 6
   浓缩concentrated
7. 7
   workup.DISSOLUTIONTo the stirring residue dissolved in THF (200 mL)
8. 8
   workup.ADDITIONwas added water (75 mL) and NaHCO3 (16.5 g)
9. 9
   workup.WAITafter 10 minutes
10. 10
    workup.STIRRINGAfter vigorous stirring for 30 minutes
11. 11
    workup.ADDITIONthe mixture was diluted with ethyl acetate
12. 12
    洗涤washed with water and brine
13. 13
    干燥dried over MgSO4
14. 14
    浓缩concentrated to an oil
15. 15
    其他The residue was chromatographed on silica gel (20–40% EtOAc/hexane)

实验过程

To a stirred solution of 5-5 (4.23 g, 21 mmol) in degassed THF (20 mL) at 0° C. was added dropwise a solution of 9-BBN (50.4 mL of 0.5 M in THF, 25.2 mmol) and the mixture stirred for 18 hours at ambient temperature. K2CO3 (5.0 g, 35.8 mmol) and 5-2 (5.0 g, 17.4 mmol) were added, followed by a premixed and aged (70° C. for 30 min) suspension of Pd(OAc)2 (0.54 g, 2.4 mmol) and DPPF (1.45 g, 2.6 mmol) in degassed DMF (20 mL). The resulting mixture was stirred for 18 hours at 70° C., cooled, diluted with ethyl acetate, washed with water and brine, dried over MgSO4, and concentrated. To the stirring residue dissolved in THF (200 mL) was added water (75 mL) and NaHCO3 (16.5 g) and after 10 minutes, NaBO3.H2O (24 g). After vigorous stirring for 30 minutes, the mixture was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, and concentrated to an oil. The residue was chromatographed on silica gel (20–40% EtOAc/hexane) to give 5-6 as a yellow solid.

来源