반응 #1532252

반응 방정식

Sodium hydride

benzyl bromide

7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

→

titled compound

수율 17.6%

1-benzyl-7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

수율 17.6%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONice was added
2. 2
   추출The reaction mixture was extracted with ethyl acetate
3. 3
   건조The separated organic layer was dried on anhydrous magnesium sulfate
4. 4
   농축concentrated under reduced pressure
5. 5
   기타The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5
6. 6
   workup.DISSOLUTIONThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
7. 7
   여과filtered

실험 절차

Sodium hydride (60%; 40 mg, 0.999 mmol) and benzyl bromide (0.475 ml, 0.399 mmol) were added at 0° C. to a solution of 7-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride (92,3 mg, 0.333 mmol) prepared in Example 468 in anhydrous tetrahydrofuran (10 ml). The reaction mixture was stirred for 12 hours at room temperature and ice was added thereto. The reaction mixture was extracted with ethyl acetate. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 23.7 mg of the titled compound as a white solid.

출처