تفاعل #1269887

معادلة التفاعل

NaOH

2-Butyl-5-hydroxyisoindolin-1-one

K2CO3

(2,6-dimethyl-4-phenylpyridin-3-yl)methyl methanesulfonate

→

2-butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methoxy)isoindolin-1-one

المردود 19.6%

المذيبات

water

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   استخلاصThe reaction mixture was extracted with EtOAc
3. 3
   غسيلthe combined organic layers were washed with water
4. 4
   تجفيفdried with MgSO4
5. 5
   أخرىthe solvent was removed in vacuo
6. 6
   أخرىPurification by flash chromatography (DCM/MeOH, gradient 1-5% MeOH)

الإجراء التجريبي

2-Butyl-5-hydroxyisoindolin-1-one (366 mg, 1.78 mmol), K2CO3 (493 mg, 3.57 mmol) and KI (296 mg, 1.78 mmol) were added to a solution of (2,6-dimethyl-4-phenylpyridin-3-yl)methyl methanesulfonate (520 mg, 1.78 mmol) in DMF (18 mL). After stirring overnight at room temperature (rt), water was added and the pH was adjusted to 13-14 using aqueous NaOH (1 M). The reaction mixture was extracted with EtOAc, the combined organic layers were washed with water, dried with MgSO4 and the solvent was removed in vacuo. Purification by flash chromatography (DCM/MeOH, gradient 1-5% MeOH) provided 2-butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methoxy)isoindolin-1-one (140 mg, 19%). ESI-MS [M+H]+=401.2.

المصدر