تفاعل #1356988

معادلة التفاعل

1H-indazol-5-ol

4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanol

triphenylphosphine

dibenzyl azodicarboxylate

→

5-{[4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]oxy}-1H-indazole

المردود 41.5%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىthe mixture thus obtained
2. 2
   تركيزthe reaction solution was concentrated under reduced pressure
3. 3
   workup.ADDITIONa 1M-aqueous sodium hydroxide solution (50 ml) was added to the resulting residue
4. 4
   استخلاصfollowed by extraction with chloroform (50 ml×2)
5. 5
   غسيلThe organic layer was washed with a saturated aqueous sodium chloride solution
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   أخرىThe organic layer dried
8. 8
   تركيزwas concentrated under reduced pressure
9. 9
   أخرىthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

الإجراء التجريبي

To a solution of the 1H-indazol-5-ol (250 mg) obtained in Reference Example 4 in tetrahydrofuran (15 ml) were added 4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanol (373 mg, 1.86 mmol), triphenylphosphine (538 mg, 2.05 mmol) and dibenzyl azodicarboxylate (667 mg, 2.24 mmol) at 0° C. After 1 hour, the mixture thus obtained was heated to room temperature. After stirring overnight, the reaction solution was concentrated under reduced pressure, and a 1M-aqueous sodium hydroxide solution (50 ml) was added to the resulting residue, followed by extraction with chloroform (50 ml×2). The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 5-{[4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]oxy}-1H-indazole (244 mg, 41%).

المصدر