تفاعل #1356981

معادلة التفاعل

acetic acid

5-(piperidin-4-yloxy)-1H-indazole

sodium hydrogencarbonate

sodium cyanoborohydride

sodium cyanoborohydride

acetic acid

→

5-[(1-isopropylpiperidin-4-yl)oxy]-1H-indazole

المردود 31.0%

المذيبات

acetone

methanol

water

acetone

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 3 days
2. 2
   استخلاصextracted with chloroform (20 ml×3)
3. 3
   تجفيفThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   أخرىThe organic layer dried
5. 5
   تركيزwas concentrated under reduced pressure
6. 6
   أخرىthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol (1%-aqueous ammonia))

الإجراء التجريبي

The 5-(piperidin-4-yloxy)-1H-indazole (80 mg, 0.368 mmol) obtained in Example 42 was suspended in methanol (2 ml), and acetone (0.031 ml, 1.10 mmol) and acetic acid (0.105 ml, 1.84 mmol) were added dropwise thereto. Then, sodium cyanoborohydride (116 mg, 1.84 mmol) was added thereto. After 18 hours, acetone, acetic acid and sodium cyanoborohydride were further added in the same amounts, respectively, as above. After 3 days, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the resulting mixture was poured into water (20 ml) and extracted with chloroform (20 ml×3). The organic layer was 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: chloroform/methanol→chloroform/methanol (1%-aqueous ammonia)) to obtain 5-[(1-isopropylpiperidin-4-yl)oxy]-1H-indazole (30 mg, 31%).

المصدر