تفاعل #2468022

معادلة التفاعل

iodine

tert-butyl [1-(6,8-difluoro[1,2,4]triazolo[4,3-a]pyridin-3-yl)-1-methylethyl]carbamate

LiHMDS

→

title compound

المردود 53.0%

tert-Butyl [1-(6,8-difluoro-7-iodo[1,2,4]triazolo[4,3-a]pyridin-3-yl)-1-methylethyl]carbamate

المردود 53.0%

المذيبات

tetrahydrofuran

tetrahydrofuran

sodium bisulphite

ammonia chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىat −78° C.
2. 2
   workup.STIRRINGThe resulting mixture was stirred at −78° C. for 2 hours
3. 3
   درجة الحرارةwarmed to 0° C.
4. 4
   درجة الحرارةIt was warmed to room temperature
5. 5
   استخلاصextracted with ethyl acetate
6. 6
   تجفيفdried over anhydrous sodium sulphate
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىThe crude was purified by silica flash chromatography
9. 9
   غسيلeluting with hexanes/ethyl acetate

الإجراء التجريبي

To a solution of tert-butyl [1-(6,8-difluoro[1,2,4]triazolo[4,3-a]pyridin-3-yl)-1-methylethyl]carbamate (1.32 g, 4.23 mmol) in tetrahydrofuran (20 mL) under argon atmosphere and at −78° C. was slowly added LiHMDS (1M in hexanes, 9.3 mL, 9.3 mmol). It was stirred at −78° C. for 45 min, afterwards a solution of iodine (1.13 g, 4.44 mmol) in tetrahydrofuran (10 mL) was added dropwise. The resulting mixture was stirred at −78° C. for 2 hours, warmed to 0° C. and diluted with aqueous sodium bisulphite (10 mL) and saturated ammonia chloride (10 mL). It was warmed to room temperature, extracted with ethyl acetate, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude was purified by silica flash chromatography eluting with hexanes/ethyl acetate, using a gradient from 50% to 83% of ethyl acetate to yield the title compound (0.979 g, 53%) as a yellow solid.

المصدر