反応 #73101

反応方程式

NIS

TFA

NIS

2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)thiazole

→

2-(4-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)thiazole

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他The crude reaction mixture
2. 2
   その他was slowly quenched with ˜30 mL of a saturated aqueous Na2S2O3 solution, and ˜30 mL of a saturated aqueous NaHCO3 solution
3. 3
   workup.ADDITIONThe reaction mixture was diluted with 50 mL of EtOAc
4. 4
   その他the layers were separated
5. 5
   抽出the aqueous layer was extracted with EtOAc (2×50 mL)
6. 6
   その他The organic layer was purified by MPLC (eluted with 0-50% EtOAc/hex)

実験手順

To a stirring mixture of 2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)thiazole (Compound 2-BA-1) in 50 mL of acetonitrile at rt under nitrogen were added TFA (1 mL) and NIS (10.8 g). The reaction mixture was stirred at rt overnight and an additional amount of NIS (0.5 eq to 1.0 eq) was added as needed. The crude reaction mixture was slowly quenched with ˜30 mL of a saturated aqueous Na2S2O3 solution, and ˜30 mL of a saturated aqueous NaHCO3 solution. The reaction mixture was diluted with 50 mL of EtOAc, the layers were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organic layer was purified by MPLC (eluted with 0-50% EtOAc/hex) to give 2-(4-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)thiazole (Compound 4-BA-1). LCMS: 408.0 m/z (M+H)+.

出典