تفاعل #794454

معادلة التفاعل

Diisopropyl azodicarboxylate

1-Cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

benzyl (trans-3-hydroxycyclobutyl)carbamate

triphenylphosphine

→

benzyl (trans-3-(1-cyclopropyl-2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)cyclobutyl)carbamate

المردود 78.0%

المذيبات

sodium bicarbonate

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was warmed to room temperature
2. 2
   استخلاصextracted with EtOAc
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwashed with saturated aqueous sodium chloride
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe resulting crude product was purified by silica gel column chromatography
9. 9
   غسيلeluting with EtOAc in hexanes

الإجراء التجريبي

1-Cyclopropyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.740 g, 4.22 mmol), benzyl (trans-3-hydroxycyclobutyl)carbamate (0.934 g, 4.22 mmol), and triphenylphosphine (1.661 g, 6.33 mmol) were mixed in THF (15 mL) under an argon atmosphere and cooled to 0° C. Diisopropyl azodicarboxylate (1.244 mL, 6.33 mmol) was added dropwise via syringe, and the reaction mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was diluted with saturated aqueous sodium bicarbonate and extracted with EtOAc. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography eluting with EtOAc in hexanes to yield benzyl (trans-3-(1-cyclopropyl-2-oxo-1H-imidazo[4,5-b]pyridin-3(2H)-yl)cyclobutyl)carbamate (1.244 g, 3.29 mmol, 78% yield) as an off-white solid. M+1: 379.2.

المصدر