تفاعل #73101

معادلة التفاعل

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

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe crude reaction mixture
2. 2
   أخرىwas 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
   أخرىthe layers were separated
5. 5
   استخلاصthe aqueous layer was extracted with EtOAc (2×50 mL)
6. 6
   أخرىThe organic layer was purified by MPLC (eluted with 0-50% EtOAc/hex)

الإجراء التجريبي

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)+.

المصدر