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

HRID 1445069노트

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HRID 1445069 반응식
[CH3:1][C:2]([Mg]Br)=[CH:3][CH3:4].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:17]1[C:22]([N+:23]([O-])=O)=[CH:21][CH:20]=[CH:19][N:18]=1.[Cl-:26].[NH4+]>O1CCCC1>[ClH:26].[CH2:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][N:8]1[C:17]1[N:18]=[CH:19][CH:20]=[C:21]2[C:3]([CH3:4])=[C:2]([CH3:1])[NH:23][C:22]=12

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 9196247Isoquinoline, 1,2,3,4-tetrahydro-2-(3-nitro-2-pyridinyl)-HCID 178448414HCID 178448414, 화합물

생성물 1

HCID 671411697-(1,2,3,4-tetrahydroisoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine hydrochloride

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution; 112 ml) was slowly added at −78° C. to a solution of 2-(1,2,3,4-tetrahydroisoquinolin-2-yl)-3-nitropyridine (4.8 g, 18.8 mmol) prepared in Preparation 20 in anhydrous tetrahydrofuran (150 ml). The reaction mixture was stirred for 4 hours at −20° C. 20% ammonium chloride solution was added to the reaction mixture, which was then 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=1/1, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 1.3 g of the titled compound as yellow solid.

후처리

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1
  5. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  6. filtrationfiltered

출처 및 근거

ORD 기록
ord-6c014da3c88f44b6b6f5e513eb99b976
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662832B2

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