反应 #155839

反应方程式

ICl

DCM

ICl

DCM

ICl

DCM

2-(4-Isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine

→

sub-title compound

收率 87.0%

7-Iodo-2-(4-isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine

收率 87.0%

溶剂

pyridine

反应条件

后处理

1. 1
   温度to warm to ambient temperature over 16 hours
2. 2
   浓缩The reaction mixture was concentrated in vacuo
3. 3
   其他the residue partitioned between EtOAc and saturated aqueous Na2CO3/saturated aqueous Na2S2O3 (1:1)
4. 4
   萃取The aqueous layer was extracted with EtOAc (100 mL)
5. 5
   洗涤the combined organic extracts washed with saturated aqueous Na2CO3/saturated aqueous Na2S2O3 (1:1) (5×50 mL)
6. 6
   干燥dried (MgSO4)
7. 7
   过滤filtered
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The residue was triturated from MeCN

实验过程

2-(4-Isopropylsulfonylphenyl)-5H-pyrrolo[2,3-b]pyrazine (1 g, 3.318 mmol) was dissolved in anhydrous pyridine (20 mL) and cooled to 0° C. in an ice-bath. 1M ICl in DCM (3.484 mL, 3.484 mmol) was added slowly and the resultant solution stirred at 0° C. After 5 hours a further portion of 1M ICl in DCM (3.484 mL, 3.484 mmol) was added and the reaction allowed to warm to ambient temperature over 16 hours. A further portion of 1M ICl in DCM (3.484 mL, 3.484 mmol) was added and the reaction stirred at ambient temperature for a further 30 minutes. The reaction mixture was concentrated in vacuo and the residue partitioned between EtOAc and saturated aqueous Na2CO3/saturated aqueous Na2S2O3 (1:1). The aqueous layer was extracted with EtOAc (100 mL) and the combined organic extracts washed with saturated aqueous Na2CO3/saturated aqueous Na2S2O3 (1:1) (5×50 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated from MeCN to give the sub-title compound as a pale orange solid (1.23 g, 87% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.21 (d, 6H), 3.49 (s, 1H), 8.01 (d, 2H), 8.22 (s, 1H), 8.46 (d, 2H), 9.03 (s, 1H) and 12.71 (s, 1H) ppm; MS (ES+) 428.0.

来源